Ammonia → N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-ethynyl-L-prolinamide
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:23]([C:24]#[CH:25])[CH2:22][CH2:21][C@H:17]1[C:18](O)=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:27]1CCOCC1.ClC(OCC(C)C)=O.N.Cl>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([N:16]1[C@@H:23]([C:24]#[CH:25])[CH2:22][CH2:21][C@H:17]1[C:18]([NH2:27])=[O:19])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cold (0° C.) solution of N-(tert-butoxycarbonyl)-L-leucyl-(5R)-5-ethynyl-L-proline (2.83 mmol) and N-methyl morpholine (0.39 mL, 3.50 mmol) in THF (15 mL) was added isobutyl chloroformate (0.42 mL, 3.25 mmol). The resulting cloudy white mixture was stirred at 0° C. for 30 minutes followed by the addition of a solution of ammonia (0.5 Min dioxane, 10.0 mL, 5.0 mmol). The solution was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was diluted by the addition of 1 M HCl (100 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated to provide the titled compound.
Workup
- temperatureto warm to room temperature
- stirringstirred for 16 hours
- extractionextracted with ethyl acetate (3×100 mL)
- dry with materialThe combined organic layers were dried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e4dec92b07c849388ece3f70cecb05af
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119664B2
Reaction notes
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