Benzyloxycarbonylglycine → 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-[N-(benzyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide

HRID 651804Notes

Reaction equation

HRID 651804 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:19]([NH:21][NH2:22])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([O:34][C:35]([NH:37][CH2:38][C:39](O)=[O:40])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)C>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:19]([NH:21][NH:22][C:39](=[O:40])[CH2:38][NH:37][C:35]([O:34][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:36])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14349BenzyloxycarbonylglycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 702001082(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvalerohydrazide

Product 1

HCID 702395472(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2'-[N-(benzyloxycarbonyl)-glycinyl]-4-methylvalerohydrazideYield 90.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.15 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvalerohydrazide and 1.86 g of N-(benzyloxycarbonyl)-glycine in 8 ml of dimethylformamide was cooled to 0° C. and treated with 2.0 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. The mixture was stirred overnight at room temperature, diluted with diethyl ether and washed sequentially with 2M aqueous hydrogen chloride, 5% aqueous sodium hydrogen carbonate, water, and saturated aqueous sodium chloride. The organic phase was dried over anhydrous magnesium sulphate and evaporated to give 2.96 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-2′-[N-(benzyloxycarbonyl)-glycinyl]-4-methylvalerohydrazide in the form of a white foam.

Workup

  1. washwashed sequentially with 2M aqueous hydrogen chloride, 5% aqueous sodium hydrogen carbonate, water, and saturated aqueous sodium chloride
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-bc74ce802cd24421af031ce03119f518
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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