Ammonia → N-BOC-b-cyclohexylalanine amide
Reaction equation
[C:1]([NH:8][C@H](C(O)=O)CC1CCCCC1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N([CH2:25][CH3:26])CC)C.ClC(O[CH2:31][CH:32]([CH3:34])C)=O.[NH3:35].[CH2:36]1[CH2:40][O:39][CH2:38][CH2:37]1>CO>[C:1]([NH:8][C:40](=[O:39])[C@H:36]([CH2:37][CH:38]1[CH2:26][CH2:25][CH2:34][CH2:32][CH2:31]1)[NH2:35])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]Participants
Conditions
- Temperature
- -20 °C
Procedure
N-[N-[N-(4-(piperidin-4-yl)butanoyl)-N-ethylglycyl]aspartyl]-L-β-cyclohexyl alanine amide ##STR17##A. N-BOC-β-cyclohexylalanine (2.0 g.) and triethyl amine (1.03 ml) aredissolved together in THF (100 ml) and the solution cooled to -20° C. Isobutyl chloroformate (1.06 ml) is added and the solution stirred at -20° C. for about 30 minutes. A saturated solution of ammonia in methanol (20 ml) is added and the solution allowed to warm to room temperature and stirred at room temperature for about 18 hours. The solution is evaporated in vacuo and the residue dissolved in ethyl acetate. The ethyl acetate solution is washed with water, 5% HCl, saturated sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered and evaporated in vacuo to give N-BOC-β-cyclohexylalanine amide.
Workup
- temperatureto warm to room temperature
- stirringstirred at room temperature for about 18 hours
- customThe solution is evaporated in vacuo
- dissolutionthe residue dissolved in ethyl acetate
- washThe ethyl acetate solution is washed with water, 5% HCl, saturated sodium bicarbonate solution, water, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-48ecf49b4a9a4c6eae2cd1a4652d58ff
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866685
Reaction notes
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