Water → HCID 59382941, compound
Reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][NH:4][CH2:5][C@@H:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CCN(CC)CC.[C:31](Cl)([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].O>C(Cl)Cl>[C:17]([O:16][C:15]([NH:14][C@@H:6]([CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:5][N:4]([CH2:3][C:2]([F:22])([F:23])[F:1])[C:31](=[O:32])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:21])([CH3:20])([CH3:18])[CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl (S)-1-(2,2,2-trifluoroethylamino)-3-cyclohexylpropan-2-ylcarbamate (1.7 g, 5 mmol) and Et3N (2 mL, 15 mmol) in CH2Cl2 (20 mL) was added dropwise a solution of CbzCl (1.02 g, 6 mmol) in CH2Cl2 (10 mL) at 0° C. After stirring for an additional 2 h, water (30 mL) was added. The mixture was extracted with CH2Cl2 (2×20 mL), the organic layers were washed with brine, dried over MgSO4, and evaporated. The residue was purified by silica chromatography to obtain benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-propyl-2,2,2-trifluoroethylcarbamate (250 mg, yield 10% for 2 steps) as an oil. 1H NMR (CDCl3, 400 MHZ) δ 0.90 (m, 2 H), 1.25 (m, 4 H), 1.44 (s, 9 H), 1.70 (m, 7 H), 3.33 (m, 2 H), 3.85 (m, 3 H), 4.45 (brs, 1 H), 5.20 (s, 2 H), 7.36 (m, 5 H).
Workup
- extractionThe mixture was extracted with CH2Cl2 (2×20 mL)
- washthe organic layers were washed with brine
- dry with materialdried over MgSO4
- customevaporated
- customThe residue was purified by silica chromatography
Sources & evidence
- ORD record
- ord-8191d11e85714ee39ad999d3253653cb
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08455521B2
Reaction notes
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