Stereoselective Addition of 2-Phenyloxazol-4-yl Trifluoromethanesulfonate to N-Sulfinyl Imines: Application to the Synthesis of the HCV Protease Inhibitor Boceprevir
William J. Morris; Kiran K. Muppalla; Cameron Cowden; Richard G. Ball; Journal of Organic Chemistry 78 (2013) 706–710; doi:10.1021/jo301856f

data_4027839
_publ_section_title
;
 Stereoselective Addition of 2-Phenyloxazol-4-yl Trifluoromethanesulfonate
 to N-Sulfinyl Imines: Application to the Synthesis of the HCV Protease
 Inhibitor Boceprevir
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              706
_journal_page_last               710
_journal_paper_doi               10.1021/jo301856f
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H25 F3 N2 O5 S2'
_chemical_formula_sum            'C19 H25 F3 N2 O5 S2'
_chemical_formula_weight         482.539
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2011-10-03
_audit_creation_method           'cif4actac using mupk0110a.cif'
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   8.6963(2)
_cell_length_b                   10.4629(3)
_cell_length_c                   25.1241(7)
_cell_measurement_reflns_used    21108
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.69
_cell_measurement_theta_min      3.78
_cell_volume                     2286.00(11)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics
;
ORTEP3 (Johnson,2000), PLATON (Spek,1990),
PSPLUTO (local version of Motherwell's program)
;
_computing_publication_material  'locally developed programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.475
_diffrn_detector_type            'Oxford Diffraction Ruby CCD'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            47273
_diffrn_reflns_theta_full        30.76
_diffrn_reflns_theta_max         30.69
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    none
_exptl_crystal_description
;
very large rectangular column with many small crystallites on the surface from
solvent evap.
;
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.683
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.199
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.34
_refine_ls_abs_structure_details
;
Flack H D (1983), Acta Cryst. A39, 876-881; Hooft, Straver, and Spek J. Appl.
 Cryst. (2008) 41, 96-103
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     286
_refine_ls_number_reflns         6734
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_gt           0.030
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0360P)^2^+0.4676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.070
_refine_ls_wR_factor_ref         0.073
_reflns_number_gt                6211
_reflns_number_total             6734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301856f_si_002.cif
_cod_data_source_block           compound19
_cod_database_code               4027839