Benzyl carbazate → HCID 70238645, compound

HRID 651819Notes

Reaction equation

HRID 651819 reaction equation
[C:1]([NH:9][CH2:10][C@@H:11]([C@@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20](O)=[O:21])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:30])[NH:28][NH2:29].Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[C:1]([NH:9][CH2:10][C@@H:11]([C@@H:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([NH:29][NH:28][C:27]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:21])[C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 79242Benzyl carbazateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20658010HCID 20658010, compound

Product 1

HCID 70238645HCID 70238645, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.9 g of 2(R)-[2-benzamido-1(R)-(tert-butoxycarbonyl)ethyl]-4-methylvaleric acid in 3 ml of dry dimethylformamide was cooled to 0° C. under a nitrogen atmosphere and treated with 2.61 g of benzyl carbazate and 1.20 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was allowed to warm to room temperature and then stirred overnight. The mixture was diluted with ethyl acetate and washed in sequence with water, 2M aqueous hydrogen chloride, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride. Drying over anhydrous magnesium sulphate and evaporation gave 2.68 g of 2(R)-[2-benzamido-1(R)-(tert-butoxycarbonyl)ethyl]-2′-benzyloxycarbonyl-4-methylvalerohydrazide in the form of a white foam.

Workup

  1. washwashed in sequence with water, 2M aqueous hydrogen chloride, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  2. dry with materialDrying over anhydrous magnesium sulphate and evaporation

Sources & evidence

ORD record
ord-2e24edb327344f18b00b1fd9d6b6d82e
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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