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

HRID 2365541Notes

Reaction equation

HRID 2365541 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-62f252bf90224dc9bf3d9e813a45c42a
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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