Water → HCID 69860796, compound

HRID 2307450Notes

Reaction equation

HRID 2307450 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=2)[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br.O>C(Cl)Cl>[C:1]1([CH:7]=[CH:8][C:9]([NH:11][C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 69919454HCID 69919454, compound

Product 1

HCID 69860796HCID 69860796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-3-phenyl-N-[1-(3-methoxyphenyl)ethyl]acrylamide (100 mg) in CH2Cl2 (0.5 mL) at −78° C. was added boron tribromide (1.0 M solution in CH2Cl2, 2.14 mL). The resulting solution was warmed to room temperature and stirred at room temperature for 3 hours. Water was added, and the mixture was extracted with CH2Cl2 (three times). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to provide the title compound.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (three times)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c73ad8cbe84949fda808e0dcc23d04c0
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

Loading…