Water → 1-butoxycarbonylaminocycloprop-1-yl-carbonyl-L-leucyl-glycinamide

HRID 64781Notes

Reaction equation

HRID 64781 reaction equation
C(N(CC)CC)C.[CH2:8]([O:12][C:13]([NH:15][C:16]1([C:19]([OH:21])=O)[CH2:18][CH2:17]1)=[O:14])[CH2:9][CH2:10][CH3:11].[NH2:22][C@H:23]([C:28]([NH:30][CH2:31][C:32]([NH2:34])=[O:33])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26].O>O1CCOCC1.C(OCC)(=O)C>[CH2:8]([O:12][C:13]([NH:15][C:16]1([C:19]([NH:22][C@H:23]([C:28]([NH:30][CH2:31][C:32]([NH2:34])=[O:33])=[O:29])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:21])[CH2:17][CH2:18]1)=[O:14])[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 6993103Glycinamide, L-leucyl-HCID 131347421-Butoxycarbonylaminocyclopropane-1-carboxylic acid

Product 1

HCID 537003341-butoxycarbonylaminocycloprop-1-yl-carbonyl-L-leucyl-glycinamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.7 ml of triethylamine and 3.6 g of the N-hydroxysuccinimide ester of 1-butoxycarbonylaminocyclopropane-1-carboxylic acid were added to 2.3 g of L-leucyl-glycinamide in 30 ml of dioxane at 10° C., the reaction mixture was stirred for 1 hour at this temperature, 10 ml of water were added and the reaction was continued for 20 hours at room temperature. In the working up procedure, the mixture was taken up in ethyl acetate and the solution was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water, dried over sodium sulfate and evaporated down under reduced pressure. The residue was purified by chromatography over a silica gel column (elution with 10:1 dichloromethane/methanol) to give 3.1 g of 1-butoxycarbonylaminocycloprop-1-yl-carbonyl-L-leucyl-glycinamide.

Workup

  1. additionwere added
  2. washthe solution was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down under reduced pressure
  5. customThe residue was purified by chromatography over a silica gel column (elution with 10:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-b09bab42489e4663aa6270048be938e3
Source dataset
uspto-grants-1986_09
Patent number
US04610818

Reaction notes

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