Benzyl Bromide → tert.-Butyl-[(2S)-1-(benzyloxy)-3-phenylpropan-2-yl]carbamate
Reaction equation
[C:1]([NH:8][C@H:9]([CH2:17][OH:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:17][O:18][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:5])([CH3:7])[CH3:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
500 mg (1.99 mmol) of N-Boc-L-phenylalaninol were dissolved in 5 ml DMF and cooled down to 0° C. under argon atmosphere. Then 159 mg (3.98 mmol) of a 60% suspension of sodium hydride was added in liquid paraffin. The reaction composition then was stirred until completion of gas formation and then mixed with 260 μl (2.19 mmol) of benzyl bromide. The cooling bath was removed and the reaction composition stirred for 2 hours at RT. Afterwards, the batch was evaporated, the residue absorbed in ice water and the composition extracted with dichlormethane. The organic phase was washed with saturated saline, dried over magnesium sulphate and evaporated. The residue was purified by means of a preparative HPLC. The yield was 226 mg (33% o. th.) of the title compound.
Workup
- customThe cooling bath was removed
- stirringthe reaction composition stirred for 2 hours at RT
- customAfterwards, the batch was evaporated
- customthe residue absorbed in ice water
- extractionthe composition extracted with dichlormethane
- washThe organic phase was washed with saturated saline
- dry with materialdried over magnesium sulphate
- customevaporated
- customThe residue was purified by means of a preparative HPLC
Sources & evidence
- ORD record
- ord-49cb9d2f170e49cd892973097edc939e
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987209B2
Reaction notes
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