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_4113477
_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         'C27 H22 F4 N1 O2'
_chemical_formula_sum            'C27 H22 F7 N O2'
_chemical_formula_weight         525.471
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2002-07-02
_audit_creation_method           'cif4actac using braj099b.cif'
_cell_angle_alpha                90
_cell_angle_beta                 100.326(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.547(1)
_cell_length_b                   7.422(1)
_cell_length_c                   14.5184(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      39.76
_cell_measurement_theta_min      33.96
_cell_volume                     1224.1(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC5'
_diffrn_measurement_method       'theta/2theta scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.541838
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2395
_diffrn_reflns_theta_max         70.14
_diffrn_standards_decay_%        1.1(17)
_diffrn_standards_interval_count 400
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.07
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    none
_exptl_crystal_description       cylindrical
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.42
_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    1.057
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     331
_refine_ls_number_reflns         2395
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_gt           0.076
_refine_ls_shift/su_max          0.02
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.222
_refine_ls_wR_factor_ref         0.257
_reflns_number_gt                1696
_reflns_number_total             2395
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja027458g-2_s4.cif
_cod_data_source_block           compound_braj099b
_cod_original_cell_volume        1224.1(5)
_cod_original_formula_sum        'C27 H22 F7 N1 O2'
_cod_database_code               4113477