Diethyl Ether → HCID 15916889, compound

HRID 1388172Notes

Reaction equation

HRID 1388172 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.[CH3:22]COCC.[N+](=C)=[N-]>COCCOC>[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]([O:20][CH3:22])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 15916887HCID 15916887, compound

Product 1

HCID 15916889HCID 15916889, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Into 4 ml of 1,2-dimethoxyethane, was dissolved 450 mg (1.52 mmoles) of (S)-7-benzyloxycarbonylamino-3-hydroxyheptanoic acid. To the solution, while being cooled in ice, was added dropwise 7 ml (4.56 mmoles) of an ether solution of diazomethane. The mixture was stirred for 30 minutes and then evaporated to dryness to yield 461 mg (98% yield) of methyl (S)-7-benzyloxycarbonylamino-3-hydroxyheptanoate. [α]D21 +1°.

Workup

  1. temperatureTo the solution, while being cooled in ice
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-de0e9c63e38846ed9453ed42d78e378c
Source dataset
uspto-grants-1984_02
Patent number
US04430346

Reaction notes

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