Triethylamine → Ethyl cis-4-[(2-naphthalenylcarbonyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

HRID 1034234Notes

Reaction equation

HRID 1034234 reaction equation
[NH2:1][CH:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C.[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[C:36](Cl)=[O:37]>C(Cl)Cl>[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[C:36]([NH:1][C@H:2]1[C:6](=[O:7])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][C@H:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 19023548Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Product 1

HCID 67794323Ethyl cis-4-[(2-naphthalenylcarbonyl)amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the aminopyrrolidinone of Example S (1.54 g, 6.2 mmol) and triethylamine (1.3 ml, 9.3 mmol) in CH2Cl2 (10 ml) was added a solution of 2-naphthoyl chloride (1.18 g, 6.2 mmol) in CH2Cl2 (7 ml) dropwise via syringe. After stirring for 12 h at room temperature the reaction mixture was evaporated in vacuo to give a residue which was chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%) to give the title compound (2.5 g, 100%) as a colorless solid. Anal calcd for C24H22N2O4 : C, 71.63; H, 5.51; N, 6.96. Found C, 71.31; H, 5.45; N, 6.73. MS calcd for C24H22N2O4 402; found 402.

Workup

  1. customwas evaporated in vacuo
  2. customto give a residue which
  3. customwas chromatographed on silica gel eluting with EtOH/CH2Cl2 (2%-5%)

Sources & evidence

ORD record
ord-d124c9d2ac5840de8e16011035b16983
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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