Scalable Synthesis and Isolation of the Four Stereoisomers of Methyl 1-Amino-3-(4-bromophenyl)cyclopentanecarboxylate, Useful Intermediates for the Synthesis of S1P1 Receptor Agonists
Grier A. Wallace; Thomas D. Gordon; Martin E. Hayes; Donald B. Konopacki; Shannon R. Fix-Stenzel; Xiaolei Zhang; Pintipa Grongsaard; Kevin P. Cusack; Lisa M. Schaffter; Rodger F. Henry; Robert H. Stoffel; Journal of Organic Chemistry 74 (2009) 4886–4889; doi:10.1021/jo900376b

data_4024600
_publ_section_title
;
Scalable Synthesis and Isolation of the Four Stereoisomers of Methyl
1-Amino-3-(4-bromophenyl)cyclopentanecarboxylate, Useful Intermediates for
the Synthesis of S1P1 Receptor Agonists
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4886
_journal_page_last               4889
_journal_paper_doi               10.1021/jo900376b
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         '2(C13 H17 Br N O2), C4 H4 O6'
_chemical_formula_sum            'C30 H38 Br2 N2 O10'
_chemical_formula_weight         746.44
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.461(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.900(4)
_cell_length_b                   6.2937(17)
_cell_length_c                   16.234(4)
_cell_measurement_reflns_used    913
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.4575
_cell_measurement_theta_min      2.6305
_cell_volume                     1549.7(7)
_computing_cell_refinement       'Bruker saintplus (Bruker 1999)'
_computing_data_collection       'Bruker SMART (Bruker 2001)'
_computing_data_reduction        'Bruker saintplus (Bruker 1999)'
_computing_molecular_graphics    'ORTEP (Johnson 1976), Accelrys (2004)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXL (Sheldrick, 2000)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17980
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         1.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.676
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelapiped
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.243
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         7278
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                5476
_reflns_number_total             7278
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo900376b_si_002.cif
_cod_data_source_block           5-(1R,3S)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

2020-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P21
_cod_original_formula_moiety     'C13 H17 Br N O2, (C4 H4 O6)0.5'
_cod_original_formula_sum        'C15 H19 Br N O5'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     373.22
_cod_database_code               4024600