Water → HCID 13124491, compound

HRID 2119228Notes

Reaction equation

HRID 2119228 reaction equation
[C:1]([O:4][C@@H:5]1[N:8](C(=O)C(OC)=O)[C:7](=[O:15])[C@H:6]1[NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])(=[O:3])[CH3:2].O>CO>[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:15])[C@H:6]1[NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 13430189HCID 13430189, compound

Product 1

HCID 13124491HCID 13124491, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture containing 2.34 g (6.43 mmol) methyl ((3S,4S)-4-acetoxy-3-benzyloxycarbonylaminoazetidin-2-on-1-yl)-2-oxoacetate and 5 ml of water in 250 ml of methanol is left at room temperature for 2 days. The mixture is evaporated in vacuo and the residue dried in high vacuo and recrystallized from methylene chloride-n-hexane. In this way, 1.33 g (74%) of title compound of melting point 110° to 113° C. is obtained. Chromatography of the mother liquors on 70 g of silica gel using a 3:1 mixture of toluene and ethyl acetate (20 fractions, 70 ml each) affords 300 mg (17%) pure crystalline product, additionally. IR spectrum in methylene chloride: 3500, 1800, 1745, 1730, 1510 and 1210 cm-1.

Workup

  1. customThe mixture is evaporated in vacuo
  2. customthe residue dried in high vacuo
  3. customrecrystallized from methylene chloride-n-hexane

Sources & evidence

ORD record
ord-e6e1765775294f5eb390367d6d61ad34
Source dataset
uspto-grants-1987_07
Patent number
US04683303

Reaction notes

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