Triethylamine → 1-benzyloxycarbonylaminocyclohex-1-yl-carbonyl-L-leucyl-glycinamide

HRID 64780Notes

Reaction equation

HRID 64780 reaction equation
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([NH:19][C:20]1([C:26]([OH:28])=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[NH2:36][C@H:37]([C:42]([NH:44][CH2:45][C:46]([NH2:48])=[O:47])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40]>O1CCCC1.CN(C)C=O>[CH2:9]([O:16][C:17]([NH:19][C:20]1([C:26]([NH:36][C@H:37]([C:42]([NH:44][CH2:45][C:46]([NH2:48])=[O:47])=[O:43])[CH2:38][CH:39]([CH3:40])[CH3:41])=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 6993103Glycinamide, L-leucyl-HCID 113578861-(Cbz-amino)cyclohexanecarboxylic acid

Product 1

HCID 544495271-benzyloxycarbonylaminocyclohex-1-yl-carbonyl-L-leucyl-glycinamideYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4 ml of isobutyl chloroformate were added dropwise to 7.9 g of 1-benzyloxycarbonylaminocyclohexane-1-carboxylic acid and 4 ml of triethylamine in 75 ml of tetrahydrofuran at -10° C., while stirring, 5.6 g of L-leucyl-glycinamide in 50 ml of dimethylformamide were added to the resulting solution of the asymmetric acid anhydride after 15 minutes, and the mixture was stirred for 1 hour at -10° C. and then for 16 hours at room temperature, after which it was evaporated down under reduced pressure. The residue 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. 7.5 g of 1-benzyloxycarbonylaminocyclohex-1-yl-carbonyl-L-leucyl-glycinamide were obtained.

Workup

  1. stirringthe mixture was stirred for 1 hour at -10° C.
  2. customafter which it was evaporated down under reduced pressure
  3. washthe solution was washed successively with 10% strength aqueous citric acid solution, sodium carbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-e3d92386c0444467ba0321c7f3e02af5
Source dataset
uspto-grants-1986_09
Patent number
US04610818

Reaction notes

Loading…