Triethylamine → Ethyl cis-4-[[(3,4-dichlorophenyl)carbonyl]amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

HRID 1034231Notes

Reaction equation

HRID 1034231 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[NH2:12][CH:13]1[C:17](=[O:18])[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH:14]1[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([NH:12][C@H:13]2[C:17](=[O:18])[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][C@H:14]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:6])[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 19023548Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Product 1

HCID 67793043Ethyl cis-4-[[(3,4-dichlorophenyl)carbonyl]amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylateYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dichlorobenzoyl chloride (295 mg, 1.41 mmol) in CH2Cl2 (4 ml) was added a solution of aminopyrrolidinone of Example S (350 mg, 1.41 mmol) and triethylamine (0.4 ml, 2.82 mmol) in CH2Cl2 (4 ml) and the resulting solution was stirred for 18 h at room temperature. Concentration in vacuo gave an oil which was chromatographed on silica gel eluting with 2% EtOH/CH2Cl2 to give the title compound (400 mg, 67%) as a colorless solid. Anal calcd for C20H18N2O4Cl2 : C, 57.02; H, 4.31; N, 6.65. Found: C, 57.05; H, 4.39; N, 6.50. MS M+1 calcd for C20H18N2O4Cl2 422, found 422.

Workup

  1. concentrationConcentration in vacuo
  2. customgave an oil which
  3. customwas chromatographed on silica gel eluting with 2% EtOH/CH2Cl2

Sources & evidence

ORD record
ord-71f90f2264214e93bfb8ba94542848e6
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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