Diazomethane → HCID 15916889, compound

HRID 703375Notes

Reaction equation

HRID 703375 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([OH:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:24])=[N-]>COCCOC.CCOCC>[CH3:24][O:19][C:18](=[O:20])[CH2:17][C@@H:16]([OH:21])[CH2:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 15916887HCID 15916887, compound

Product 1

HCID 15916889HCID 15916889, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 450 mg (1.52 mmoles) of (S)-7-benzyloxycarbonylamino -3-hydroxyheptanoic acid in 1,2-dimethoxyethane, while being cooled in ice, was added dropwise 7 ml (4.56 mmoles) of a solution of diazomethane in ether. The mixture was stirred for 30 minutes. The reaction mixture was evaporated to dryness to yield 461 mg (98% yield) of (S)-7-benzyloxycarbonylamino-3-hydroxyheptanoic acid methyl ester;[α]D21 +1°.

Workup

  1. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-0722fb3b8e9c4908ba9050f046911045
Source dataset
uspto-grants-1991_01
Patent number
US04983328

Reaction notes

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