Diethyl Ether → HCID 86737603, compound

HRID 1154969Notes

Reaction equation

HRID 1154969 reaction equation
[O:1]=[C:2]1[CH2:6][CH:5]([CH:7]([N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[C:8]([O:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[O:4][NH:3]1.[N+](=[CH2:37])=[N-].CCOCC>C(Cl)Cl>[CH3:37][O:1][C:2]1[CH2:6][CH:5]([CH:7]([N:24]2[C:25](=[O:34])[C:26]3=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]3[C:28]2=[O:29])[C:8]([O:10][CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 12939894HCID 12939894, compound

Product 1

HCID 86737603HCID 86737603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 90 mg. (0.2 mmole) of 3-oxo-α-phthalimido 5-isoxazolidine acetic acid, benzhydryl ester (IIa) in 5 ml of methylene chloride is added a 50% molar excess of a standard etheral diazomethane solution. A 5 μl. amount of βF3.Et2O is added and, after 30 minutes, the reaction is concentrated and the residue chromatographed on preparative TLC (AIX eluent) to yield (45 mg.) of 3-methoxy-4,5-dihydro-α-phthalimido-5-isoxazole acetic acid, benzhydryl ester.

Workup

  1. concentrationthe reaction is concentrated
  2. customthe residue chromatographed on preparative TLC (AIX eluent)

Sources & evidence

ORD record
ord-b73c28a4eee74c15a6c6ec1993f4ccb3
Source dataset
uspto-grants-1981_11
Patent number
US04298744

Reaction notes

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