Triethylamine → diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

HRID 232212Notes

Reaction equation

HRID 232212 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.Cl[C:18]1([C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:22]=[CH:21][C:20](=[O:23])[O:19]1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:15][O:14][N:13]([C:18]3([C:24]([O:26][CH:27]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[O:25])[CH:22]=[CH:21][C:20](=[O:23])[O:19]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20030875HCID 20030875, compoundHCID 56633768(4S)-4-phenylacetamido-3-isoxazolidinone

Product 1

HCID 67902310diphenylmethyl 2-[(4S)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylateYield 71.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 2.5 ml of dichloromethane suspension of 35 mg of (4S)-4-phenylacetamido-3-isoxazolidinone and 50 mg of diphenylmethyl 2-chloro-5-oxo-2,5-dihydro-2-furancarboxylate obtained in Example 49 was added under ice-cooling and stirring, 0.025 ml of triethylamine. The reaction solution was stirred at room temperature for 30 minutes, which was diluted with ethyl acetate, followed by washed with water and drying (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 56 mg of the subject Compound (51) as colorless crystals. Recryslallization from dichloromethaneethylether afforded colorless prisms, m.p. 168°-169° C. (decomp.).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. stirringThe reaction solution was stirred at room temperature for 30 minutes
  4. washby washed with water
  5. dry with materialdrying (Na2SO4)
  6. customThe solvent was evaporated off
  7. washfollowed by elution with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-b1f80655838d4e0d9bc9002039614732
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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