Methanol → HCID 22841883, compound

HRID 1196206Notes

Reaction equation

HRID 1196206 reaction equation
[CH:1]([C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH3:11])=[CH2:4])=[O:2].[N+](=C)=[N-].C[OH:27]>C(OCC)C>[C:1]([C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH3:11])=[CH2:4])([OH:27])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 22843867HCID 22843867, compound

Product 1

HCID 22841883HCID 22841883, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(3S,4S)-4-(1-Carboxyethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (37 g), which was prepared from (3S,4S)-4-(1-formylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone in the similar procedure to Example 6, was dissolved in methanol and then diluted with diethyl ether. A solution of diazomethane in diethyl ether was added dropwise thereto with ice-cooling, and the resultant mixture was stirred for 0.5 hour. After removal of excess diazomethane, the reaction mixture was concentrated in vacuo to give (3S,4S)-4-(1-methoxycarbonylethenl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

Workup

  1. temperaturewith ice-cooling
  2. customAfter removal of excess diazomethane
  3. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3e8d889a3d4740a39f500e47ceee39d3
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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