Triethylamine → HCID 58246892, compound
Reaction equation
[NH2:1][C@@H:2]([CH3:19])[C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CCN(CC)CC.[C:27](Cl)([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>CO>[C:14]([O:13][C:12]([NH:11][C@@H:3]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C@@H:2]([NH:1][C:27](=[O:28])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:19])=[O:18])([CH3:15])([CH3:17])[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of tert-butyl (2S,3S)-3-amino-1-cyclohexylbutan-2-ylcarbamate (0.153 g, 0.57 mmol) and Et3N (0.19 mL, 1.42 mmol) in methanol (5 mL) at 0° C. was added dropwise a solution of CBZCl (0.116 g, 0.68 mmol) in methanol (3 mL). The mixture was warmed to rt, stirred 2 h, evaporated to remove methanol, diluted with water (15 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (15 mL), dried and evaporated to give benzyl (2S,3S)-3-(tert-butoxycarbonyl)amino-4-cyclohexylbutan-2-ylcarbamate (0.117 g, 51%) that was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): 7.32 (m, 5H), 5.37 (brs, 1H), 5.09 (s, 2H), 4.36 (brs (1H), 3.76 (m, 2H), 1.82 (m, 1H), 1.66 (m, 4H), 1.44 (s, 9H), 1.35-1.10 (m, 6H), 1.07 (d, J=6.4 Hz, 3H), 1.00-0.78 (m, 2H); MS (E/Z): 405 (M+H+).
Workup
- customevaporated
- customto remove methanol
- additiondiluted with water (15 mL)
- extractionextracted with EtOAc (3×10 mL)
- washThe combined organic layers were washed with brine (15 mL)
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-cf11eb2bf9e24560b5620855294359aa
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08487108B2
Reaction notes
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