Development of a Large Scale Asymmetric Synthesis of the Glucocorticoid Agonist BI 653048 BS H3PO4
Jonathan T. Reeves; Daniel R. Fandrick; Zhulin Tan; Jinhua J. Song; Sonia Rodriguez; Bo Qu; Soojin Kim; Oliver Niemeier; Zhibin Li; Denis Byrne; Scot Campbell; Ashish Chitroda; Phil DeCroos; Thomas Fachinger; Victor Fuchs; Nina C. Gonnella; Nelu Grinberg; Nizar Haddad; Burkhard Jäger; Heewon Lee; Jon C. Lorenz; Shengli Ma; Bikshandarkoil A. Narayanan; Larry J. Nummy; Ajith Premasiri; Frank Roschangar; Max Sarvestani; Sherry Shen; Earl Spinelli; Xiufeng Sun; Richard J. Varsolona; Nathan Yee; Michael Brenner; Chris H. Senanayake; Journal of Organic Chemistry 78 (2013) 3616–3635; doi:10.1021/jo400079z

data_4028140
_publ_section_title
;
 Development of a Large Scale Asymmetric Synthesis of the Glucocorticoid
 Agonist BI 653048 BS H3PO4
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3616
_journal_page_last               3635
_journal_paper_doi               10.1021/jo400079z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C23 H28 F4 N3 O8 P S'
_chemical_formula_weight         613.51
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3288(17)
_cell_length_b                   9.3506(19)
_cell_length_c                   33.517(7)
_cell_measurement_temperature    293(2)
_cell_volume                     2610.3(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            4035
_diffrn_reflns_theta_full        63.33
_diffrn_reflns_theta_max         63.33
_diffrn_reflns_theta_min         5.28
_exptl_absorpt_coefficient_mu    2.433
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             1272
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(17)
_refine_ls_extinction_coef       0.0066(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0458P)^2^+1.2574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                3946
_reflns_number_total             4035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400079z_si_002.cif
_cod_data_source_block           12
_cod_database_code               4028140