Diisopropylethylamine → Methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]carbamic acid benzyl ester
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]([NH:5]CCNC)=[O:4].CCN(C(C)C)C(C)C.[CH2:21]([O:28][C:29]([N:31]1[C:35](=O)[CH2:34]C[C:32]1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][C:29](=[O:30])[N:31]([CH3:32])[CH2:35][CH2:34][NH:5][C:3](=[O:4])[C:2]([F:11])([F:10])[F:1])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of compound A (96.8 g, 340.7 mmol) and DIEA (59.3 ml, 340.7 mmol) in THF (350 ml) was cooled to ˜5° C., followed by addition of a solution of N-(benzyloxycarbonyl)succinimide (84.0 g, 337.3 mmol) in THF (150 ml) dropwise over the period of 20 min The temperature of reaction mixture was raised to room temperature and stirring was continued for an additional 30 min, followed by the solvents being evaporated. The resultant residue was dissolved in EtOAc (600 ml). EtOAc was extracted with 5% aq. NaHCO3 (2×150 ml) and brine (150 ml). The organic layer was separated and evaporated to provide compound B as yellowish oil (103.0 g, 340.7 mmol). LC-MS [M+H] 305.3 (C13H15F3N2O3+H, calc: 305.3). Compound B was used without further purification.
Workup
- customThe temperature of reaction mixture
- custombeing evaporated
- dissolutionThe resultant residue was dissolved in EtOAc (600 ml)
- extractionEtOAc was extracted with 5% aq. NaHCO3 (2×150 ml) and brine (150 ml)
- customThe organic layer was separated
- customevaporated
Sources & evidence
- ORD record
- ord-b16db2e93dd04099863ae5cb0110a7db
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802681B2
Reaction notes
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