Efficient Asymmetric Synthesis of Novel Gastrin Receptor Antagonist AG-041R via Highly Stereoselective Alkylation of Oxindole Enolates
Takashi Emura; Toru Esaki; Kazutaka Tachibana; Makoto Shimizu; Journal of Organic Chemistry 71 (2006) 8559–8564; doi:10.1021/jo061541v

data_4022051
_publ_contact_author_address
;Komakado 1-135
Gotemba
SHIZUOKA 412-8513
JAPAN
;
_publ_contact_author_email       emuratks@chugai-pharm.co.jp
_publ_contact_author_fax         xx81-550-87-5326
_publ_contact_author_name        'Takeshi Emura'
_publ_contact_author_phone       xx81-550-87-3411
_publ_section_title
;
 Efficient Asymmetric Synthesis of Novel Gastrin Receptor
 Antagonist AG-041R via Highly Stereoselective Alkylation
 of Oxindole Enolates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8559
_journal_page_last               8564
_journal_paper_doi               10.1021/jo061541v
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_sum            'C30 H39 N3 O5'
_chemical_formula_weight         521.64
_space_group_IT_number           19
_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                   8.161(3)
_cell_length_b                   10.241(4)
_cell_length_c                   34.890(12)
_cell_measurement_temperature    108(2)
_cell_volume                     2916.0(19)
_computing_cell_refinement       HKL2000
_computing_data_collection       HKL2000
_computing_data_reduction        HKL2000
_computing_molecular_graphics    Mercury
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  RAXIS-V
_diffrn_radiation_monochromator  silicone
_diffrn_radiation_source         'synchrotron radiation SPring8 BL32B2'
_diffrn_radiation_wavelength     0.70000
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3810
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.063(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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+0.6361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                3770
_reflns_number_total             3810
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061541vsi20060725_082644.cif
_cod_database_code               4022051