Phenylacetic Acid → HCID 53966216, compound

HRID 1649344Notes

Reaction equation

HRID 1649344 reaction equation
[NH2:1][C:2]1([O:7][CH3:8])[CH2:5][NH:4][C:3]1=[O:6].[C:9]1([CH2:15][C:16](O)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[C:9]1([CH2:15][C:16]([NH:1][C:2]2([O:7][CH3:8])[CH2:5][NH:4][C:3]2=[O:6])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 13018965HCID 13018965, compound

Product 1

HCID 53966216HCID 53966216, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 61 mg of 3-amino-3-methoxy-2-oxoazetidine in 2 ml of THF are added 72 mg of phenylacetic acid, 71.3 mg of 1-hydroxybenzotriazole and 130 mg of dicyclohexylcarbodiimide, and the mixture is stirred at room temperature for 3 hours. The dicyclohexylurea is filtered off, and the filtrate is concentrated. The residue is chromatographed on a column of silica gel [eluted with n-hexane-ethyl acetate (1:2)] to obtain 86 mg of 3-phenylacetamido-3-methoxy-2-oxoazetidine.

Workup

  1. filtrationThe dicyclohexylurea is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is chromatographed on a column of silica gel [eluted with n-hexane-ethyl acetate (1:2)]

Sources & evidence

ORD record
ord-7b95c0564d7e401cadde4298f5f536dc
Source dataset
uspto-grants-1983_11
Patent number
US04416817

Reaction notes

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