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

HRID 1034236Notes

Reaction equation

HRID 1034236 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][CH:12]1[C:16](=[O:17])[N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH:13]1[C:24]([O:26][CH2:27][CH3:28])=[O:25].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C@H:12]2[C:16](=[O:17])[N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][C@H:13]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 19023548Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Product 1

HCID 67794583Ethyl cis-4-[[(4-chlorophenyl)carbonyl]amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylateYield 69.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of p-chlorobenzoyl chloride (247 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 5/95 EtOH/CH2Cl2 to give the title compound (378 mg, 68%) as a solid. Anal calcd for C20H19N2O4Cl; C, 62.10; H, 4.95; N, 7.24. Found: C, 62.07; H, 5.05; N, 7.18. MS calcd for C20H19N2O4Cl 386, found 386. DSC=215.2°-216.8° C. at 144.3 J/g.

Workup

  1. concentrationConcentration in vacuo
  2. customgave an oil which
  3. customwas chromatographed on silica gel eluting with 5/95 EtOH/CH2Cl2

Sources & evidence

ORD record
ord-27c0640d5f244a389294d6499697409d
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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