Boron tribromide → N-formyl-3,4-dihydroxy-6-iodo-L-phenylalanine ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C@H:5]([CH2:9][C:10]1[C:15]([I:16])=[CH:14][C:13]([O:17]C)=[C:12]([O:19]C)[CH:11]=1)[NH:6][CH:7]=[O:8])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:21])[C@H:5]([CH2:9][C:10]1[C:15]([I:16])=[CH:14][C:13]([OH:17])=[C:12]([OH:19])[CH:11]=1)[NH:6][CH:7]=[O:8])[CH3:2]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
To a solution of iodo derivative 3 (2 g, 4.9 mmol) in methylene chloride (35 mL) cooled in a -78° C. bath was added BBr3 (17.5 mL of 1M solution in methylene chloride) and the mixture was stirred at -78° C. for 15 min. The cooling bath was removed and the stirring continued until the mixture reached ambient temperature (~30 min). Finally, the reaction mixture was poured into ice water (100 mL), stirred at room temperature for 30 min. and the methylene chloride layer was separated. Evaporation of methylene chloride under reduced pressure resulted in a pale yellow solid 4 (1.2 g, 65%) m.p. 131°-132° C.
Workup
- customThe cooling bath was removed
- customreached ambient temperature
- custom(~30 min)
- additionFinally, the reaction mixture was poured into ice water (100 mL)
- stirringstirred at room temperature for 30 min.
- customthe methylene chloride layer was separated
- customEvaporation of methylene chloride under reduced pressure
Sources & evidence
- ORD record
- ord-1e7f95337e1c4ab5a5465997363b2443
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05393908
Reaction notes
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