Ammonia → 8-Benzyloxycarbonylamino-3-hydroxyoctanamide

HRID 703379Notes

Reaction equation

HRID 703379 reaction equation
[NH3:1].C([O:4][C:5](=O)[CH2:6][CH:7]([OH:24])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])C>CO>[CH2:17]([O:16][C:14]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:7]([OH:24])[CH2:6][C:5]([NH2:1])=[O:4])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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 methanol saturated with gaseous ammonia was dissolved 1.69 g (5 mmoles) of ethyl8-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-b225c37bb80844efa34c10a534485f24
Source dataset
uspto-grants-1991_01
Patent number
US04983328

Reaction notes

Loading…