Benzyl Bromide → N-benzyloxycarbonylphenylalanine methyl ester
Reaction equation
O1CCCC1.[CH3:6][O:7][C:8](=[O:24])[C@H:9]([CH:21]([CH3:23])C)[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].C(Br)[C:26]1[CH:31]=[CH:30]C=[CH:28][CH:27]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH3:6][O:7][C:8](=[O:24])[C@H:9]([CH2:21][C:23]1[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=1)[NH:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a tetrahydrofuran solution (1 ml) of the compound prepared in Example 6 (174 mg, 0.5 mmol), were succcessively added dropwise at 0° C. in a nitrogen atmosphere benzyl bromide (0.119 ml, 1.0 mmol) and a tetrahydrofuran solution of tetrabutyl ammonium fluoride (0.5 ml, 0.5 mmol). After the mixture was stirred for 1 hour at 0° C., it was poured into water and extracted with ether. The ether layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The resulting reaction mixture was subjected to column chromatography on silica gel and eluted with a 3:7 mixture of ether and hexane to give the titled compound in an amount of 122 mg (yield, 78% based on the starting materials used in Example 6)
Workup
- extractionextracted with ether
- dry with materialThe ether layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under vacuum
- customThe resulting reaction mixture
- washeluted with a 3:7 mixture of ether and hexane
Sources & evidence
- ORD record
- ord-52d7808edc8f4968a1a36d00b4c16049
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04837349
Reaction notes
Loading…