Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids
Blanca R. Díaz-Sánchez; Martín A. Iglesias-Arteaga; Roberto Melgar-Fernández; Eusebio Juaristi; Journal of Organic Chemistry 72 (2007) 4822–4825; doi:10.1021/jo0705115

data_4023953
_publ_contact_author_address
;     Departamento de Qu\'imica
      Centro de Investigaci\'on y de Estudios Avanzados
      Instituto Polit\'ecnico Nacional
      Apartado Postal 14-740      
      07000 M\'exico D.F.
      Mexico
;
_publ_contact_author_email       juaristi@relaq.mx
_publ_contact_author_fax         (+52)(55)57477132
_publ_contact_author_name        'Eusebio Juaristi'
_publ_contact_author_phone       (+52)(55)50613722
_publ_section_title
;
 Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones
 and Their Derivatization Utilizing the Sonogashira Coupling Reaction
 in the Enantioselective Synthesis of \a-Substituted
 \b-Amino Acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4822
_journal_page_last               4825
_journal_paper_doi               10.1021/jo0705115
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C14 H15 Br1 N2 O2'
_chemical_formula_sum            'C14 H15 Br N2 O2'
_chemical_formula_weight         323.19
_chemical_melting_point          469
_chemical_name_systematic
;
1-Benzoyl-2(S)-iso-propyl-5-bromo-2,3-dihydro-4(H)-pyrimidin-4-one
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-12-07
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.9920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4454(4)
_cell_length_b                   7.2110(2)
_cell_length_c                   14.2431(5)
_cell_measurement_reflns_used    2974
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.395
_cell_volume                     1426.23(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5145
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         5145
_exptl_absorpt_coefficient_mu    2.882
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.864
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(12)
_refine_ls_extinction_coef       0.0106(12)
_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   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.1706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2647
_reflns_number_total             2842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705115si20070313_011453_2.cif
_cod_data_source_block           ejbd02
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4023953