Efficient Synthesis of NK1 Receptor Antagonist Aprepitant Using a Crystallization-Induced Diastereoselective Transformation
Karel M. J. Brands; Joseph F. Payack; Jonathan D. Rosen; Todd D. Nelson; Alexander Candelario; Mark A. Huffman; Matthew M. Zhao; Jing Li; Bridgette Craig; Zhiguo J. Song; David M. Tschaen; Karl Hansen; Paul N. Devine; Philip J. Pye; Kai Rossen; Peter G. Dormer; Robert A. Reamer; Christopher J. Welch; David J. Mathre; Nancy N. Tsou; James M. McNamara; Paul J. Reider; Journal of the American Chemical Society 125 (2003) 2129–2135; doi:10.1021/ja027458g

data_4113475
_publ_section_title
;
 Efficient Synthesis of NK1 Receptor Antagonist Aprepitant Using a
 Crystallization-Induced Diastereoselective Transformation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2129
_journal_page_last               2135
_journal_paper_doi               10.1021/ja027458g
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C21 H19 F6 N1 O3'
_chemical_formula_sum            'C21 H19 F6 N O3'
_chemical_formula_weight         447.381
_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             2002-07-02
_audit_creation_method           'cif4actac using braj099a.cif'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.644(2)
_cell_length_b                   17.879(2)
_cell_length_c                   9.382(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      39.96
_cell_measurement_theta_min      38.08
_cell_volume                     2120.9(5)
_computing_cell_refinement       'Molecular Structure Corp. AFC5 software'
_computing_data_collection       'Molecular Structure Corp. AFC5 software'
_computing_data_reduction        'locally developed software'
_computing_molecular_graphics
'ORTEP (Johnson, 1965) & PLUTO (Motherwell and Clegg)'
_computing_publication_material  'locally developed software'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_measurement_device       'Rigaku AFC5 diffractometer'
_diffrn_measurement_method       'theta/2theta scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.541838
_diffrn_reflns_av_R_equivalents  0.
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2051
_diffrn_reflns_theta_max         72.57
_diffrn_standards_decay_%        -2.5(9)
_diffrn_standards_interval_count 400
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.10
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    none
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.70
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2047
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_gt           0.128
_refine_ls_shift/su_max          -0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+( 0.2417P)^2^+3.2209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.315
_reflns_number_gt                1524
_reflns_number_total             2051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja027458g-2_s2.cif
_cod_data_source_block           compound_braj099a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(
0.2417P)^2^+3.2209P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[\s^2^(Fo^2^)+( 0.2417P)^2^+3.2209P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2121.0(7)
_cod_original_formula_sum        'C21 H19 F6 N1 O3'
_cod_database_code               4113475