Synthesis of 1,3,5-trisubstituted hydantoins by regiospecific domino condensation/aza-Michael/O-N acyl migration of carbodiimides with activated α,β-carboxylic acids
A.Volonterio; C. Ramirez de Arellano; M. Zanda; Journal of Organic Chemistry 70 (2005) 2161–2170; doi:10.1021/jo0480848

data_4020150
_publ_section_title
;
Synthesis of 1,3,5-trisubstituted hydantoins by regiospecific
domino condensation/aza-Michael/O-N acyl migration of carbodiimides
with activated \a,\b-carboxylic acids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2161
_journal_page_last               2170
_journal_paper_doi               10.1021/jo0480848
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C16 H25 F3 N2 O4'
_chemical_formula_weight         366.38
_chemical_name_systematic
;
2-(1,3-Di-tert-butyl-2,5-dioxo-imidazolidin-4-yl)-3,3,3-trifluoro-propionic
acid ethyl ester
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.838(2)
_cell_length_b                   11.258(2)
_cell_length_c                   17.227(3)
_cell_measurement_reflns_used    10426
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1832.7(6)
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \w-scans
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17225
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.62
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.48
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0609P)^2^+0.4789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                3727
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4020150