Ammonia → 8-Benzyloxycarbonylamino-3-hydroxyoctanamide

HRID 462903Notes

Reaction equation

HRID 462903 reaction equation
[NH3:1].[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([OH:25])[CH2:19][C:20](OCC)=[O:21])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([OH:25])[CH2:19][C:20]([NH2:1])=[O:21])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13457290Ethyl 8-benzyloxycarbonylamino-3-hydroxyoctanoate

Product 1

HCID 134572918-Benzyloxycarbonylamino-3-hydroxyoctanamideYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into 40 ml of methanol saturated with gaseous ammonia was dissolved 1.69 g (5 mmoles) of ethyl 8-benzyloxycarbonylamino-3-hydroxyoctanoate. The solution was stirred for 3 days at room temperature, and the reaction mixture was evaporated to dryness. The residue was crystallized from ethanol to yield 1.18 g (72.5% yield) of 8-benzyloxycarbonylamino-3-hydroxyoctanamide having a melting point of 100°-101° C.

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-af495b684f7a40a6ba419abe35e409fa
Source dataset
uspto-grants-1985_05
Patent number
US04518532

Reaction notes

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