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_4113476
_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 F7 N O2'
_chemical_formula_sum            'C27 H22 F7 N O2'
_chemical_formula_weight         525.46
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.806(6)
_cell_angle_beta                 98.216(6)
_cell_angle_gamma                103.386(6)
_cell_formula_units_Z            2
_cell_length_a                   9.098(4)
_cell_length_b                   9.876(4)
_cell_length_c                   14.495(6)
_cell_measurement_temperature    298(2)
_cell_volume                     1209.3(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9740
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plates
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                3418
_reflns_number_total             4886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja027458g-2_s3.cif
_cod_data_source_block           djm0921m
_cod_original_cell_volume        1209.5(8)
_cod_database_code               4113476