Conversion of a Benzofuran Ester to an Amide through an Enamine Lactone Pathway: Synthesis of HCV Polymerase Inhibitor GSK852A.
Bowman, Roy K.; Bullock, Kae M.; Copley, Royston C. B.; Deschamps, Nicole M.; McClure, Michael S.; Powers, Jeremiah D.; Wolters, Andy M.; Wu, Lianming; Xie, Shiping; The Journal of organic chemistry 80 (2015) 9610–9619; doi:10.1021/acs.joc.5b01598

data_4036332
_publ_section_title
;
 Conversion of a Benzofuran Ester to an Amide through an Enamine Lactone
 Pathway: Synthesis of HCV Polymerase Inhibitor GSK852A.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9610
_journal_page_last               9619
_journal_paper_doi               10.1021/acs.joc.5b01598
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H15 F N2 O4'
_chemical_formula_sum            'C19 H15 F N2 O4'
_chemical_formula_weight         354.33
_chemical_name_systematic
;
(3Z)-5-Cyclopropyl-3-[(4-fluorophenyl)(methylamino)methylidene]-
6-nitro-1-benzofuran-2(3H)-one
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.377(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9217(15)
_cell_length_b                   20.462(6)
_cell_length_c                   9.881(2)
_cell_measurement_reflns_used    371
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      51.30
_cell_measurement_theta_min      2.16
_cell_volume                     1575.5(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics    'SHELXTL V2008/4 (Bruker, 2008)'
_computing_publication_material  'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_refinement  'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_solution    'SHELXTL V2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   44.00   72.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        0.6250  179.0000    0.0000 28

  2 omega   47.00   73.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        0.6250  179.0000 -120.0000 26

  3 omega   39.00   68.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -        0.6250  179.0000   90.0000 29

  4 omega  -47.00  -21.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.4177   38.0000  120.0000 26

  5 omega  -11.00   14.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.4177   38.0000  120.0000 25

  6 omega  -10.00   16.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       62.6677  -38.0000  -30.0000 26

  7 omega   35.00  134.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       62.6677   47.0000 -114.0000 99

  8 omega   80.00  114.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       62.6677  125.0000   90.0000 34

  9 omega   78.00  126.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       62.6677  125.0000  150.0000 48

 10 omega    5.00   70.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       62.6677  -38.0000   90.0000 65
;
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_UB_11      0.0303798000
_diffrn_orient_matrix_UB_12      -0.0436229000
_diffrn_orient_matrix_UB_13      0.1293645000
_diffrn_orient_matrix_UB_21      0.1907986000
_diffrn_orient_matrix_UB_22      -0.0067455000
_diffrn_orient_matrix_UB_23      -0.0112684000
_diffrn_orient_matrix_UB_31      0.0425219000
_diffrn_orient_matrix_UB_32      0.0609150000
_diffrn_orient_matrix_UB_33      0.0909390000
_diffrn_radiation_collimation    '0.8 mm double-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_av_sigmaI/netI    0.1841
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2721
_diffrn_reflns_theta_full        44.46
_diffrn_reflns_theta_max         44.46
_diffrn_reflns_theta_min         4.32
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.34.49 
(release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25)

Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     'SHELXTL V2008/4 (Bruker, 2008)'
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         1241
_refine_ls_number_restraints     247
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                576
_reflns_number_total             1241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01598_si_001.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_geom_angle_publ_flag' value 'Y' was changed to 'y' in
accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26 (43 times).

data item '_geom_bond_publ_flag' value 'Y' was changed to 'y' in
accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26 (29 times).

data item '_geom_torsion_publ_flag' value 'Y' was changed to 'y' in
accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26 (58 times).

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036332