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 (88.2 g, 311 mmol) and DIEA (54.1 mL, 311 mmol) in THF (350 mL) was cooled in an ice bath, followed by the addition of a solution of N-(benzyloxycarbonyl)succinimide (76.6 g, 307 mmol) in THF (150 mL) drop wise over the period of 20 min. The temperature of the reaction mixture was raised to ambient temperature and stirring was continued for an additional 30 min. Solvents were then evaporated and the resulting residue was dissolved in EtOAc (600 mL). The organic layer was extracted with 5% aq. NaHCO3 (2×150 mL) and brine (150 mL). The organic layer was evaporated to provide compound B as yellowish oil. LC-MS [M+H] 305.1 (C13H15F3N2O3+H, calc: 305.3). Compound B was used directly in the next reaction without purification as a MeOH solution.
Workup
- customSolvents were then evaporated
- dissolutionthe resulting residue was dissolved in EtOAc (600 mL)
- extractionThe organic layer was extracted with 5% aq. NaHCO3 (2×150 mL) and brine (150 mL)
- customThe organic layer was evaporated
Sources & evidence
- ORD record
- ord-667c560b500547eba3fb5011abfbfb01
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040032B2
Reaction notes
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