Ammonia → ((S)-4-Amino-4-carbamoyl-butyl)-carbamic acid benzyl ester

HRID 2281613Notes

Reaction equation

HRID 2281613 reaction equation
CO[C:3](=[O:20])[C@@H:4]([NH2:19])[CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[NH3:21]>CO>[CH2:12]([O:11][C:9](=[O:10])[NH:8][CH2:7][CH2:6][CH2:5][C@H:4]([NH2:19])[C:3](=[O:20])[NH2:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 7018807(S)-2-Amino-5-benzyloxycarbonylamino-pentanoic acid methyl ester

Product 1

HCID 67086977((S)-4-Amino-4-carbamoyl-butyl)-carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-Amino-5-benzyloxycarbonylamino-pentanoic acid methyl ester (2.80 g, 9.99 mmol) and 7M NH3 in MeOH (20 ml) is stirred at room temperature for 72 hours. The reaction mixture is evaporated to dryness in vacuo to yield a white solid. The white solid is suspended in diethyl ether before filtration and drying to yield ((S)-4-Amino-4-carbamoyl-butyl)-carbamic acid benzyl ester.

Workup

  1. customThe reaction mixture is evaporated to dryness in vacuo
  2. customto yield a white solid
  3. filtrationThe white solid is suspended in diethyl ether before filtration
  4. customdrying

Sources & evidence

ORD record
ord-a215e9237a8b400abd4c8ae6f311502e
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

Loading…