2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → 4-nitrobenzyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-3-(2acetamidoethylthio)-5-oxo-2-tetrahydrofurancarboxylate

HRID 232219Notes

Reaction equation

HRID 232219 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][NH:13][C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([NH:20][CH2:21][CH2:22][S:23][CH:24]([CH2:40][C:41]([O-:43])=[O:42])[C:25](=O)[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:27])(=[O:19])[CH3:18].C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C>ClCCl>[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:25]3([C:26]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=4)=[O:27])[CH:24]([S:23][CH2:22][CH2:21][NH:20][C:17](=[O:19])[CH3:18])[CH2:40][C:41](=[O:42])[O:43]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 56633768(4S)-4-phenylacetamido-3-isoxazolidinoneHCID 67901886HCID 67901886, compound

Product 1

HCID 679022754-nitrobenzyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-3-(2acetamidoethylthio)-5-oxo-2-tetrahydrofurancarboxylateYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5 ml of dichloromethane were suspended 48 mg of (4S)-4-phenylacetamido-3-isoxazolidinone and 95 mg of the Compound (70) obtained in Example 70. To the suspension was added 71 mg of 1-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The mixture was stirred for 5.5 hours at room temperature. The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with ethyl acetate to give 75 mg of the subject Compound (71) as a colorless oily product.

Workup

  1. customThe solvent was evaporated off
  2. washfollowed by elution with ethyl acetate

Sources & evidence

ORD record
ord-38b7c90d32a643a0bdcd277cb8efddfe
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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