Water → (S)-2-hydroxy-N,3-bis(4-hydroxyphenyl)-2-methylpropanamide
Reaction equation
[OH:1][C@@:2]([CH3:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=1)[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[CH:8][CH:7]=1)=[O:4].B(Br)(Br)Br.O.CCOC(C)=O>C(Cl)Cl>[OH:1][C@@:2]([CH3:23])([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:4]Participants
Procedure
(S)-2-hydroxy-N,3-bis(4-methoxyphenyl)-2-methylpropanamide (6c) (0.20 g, 0.63 mmol) was dissolved in dry CH2Cl2 (20 mL). BBr3 (6 mL of 1.0 M CH2Cl2 solution) was added dropwise with stirring via a syringe at room temperature. The reaction solution was allowed to stir overnight at room temperature. The mixture was cooled to 0° C. in a ice bath and hydrolyzed by adding water (25 mL). EtOAc (50 mL) was added to partition the solution. The organic layer was separated; the aqueous layer was extracted with EtOAc (2×10 mL). The organic layers were combined, washed with brine and dried over anhydrous MgSO4. The solvent was removed under vacuum. The residue was purified by flash column chromatography using silica-gel with hexanes/EtOAc (3/7 v/v) to afford a white solid product, (S)-2-hydroxy-N,3-bis(4-hydroxyphenyl)-2-methylpropanamide (6g), 0.12 g, 65.6% yield.
Workup
- stirringto stir overnight at room temperature
- temperatureThe mixture was cooled to 0° C. in a ice bath
- customto partition the solution
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
- washwashed with brine
- dry with materialdried over anhydrous MgSO4
- customThe solvent was removed under vacuum
- customThe residue was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-da57f03d0f1842b2bc80e6778ed3327c
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158828B2
Reaction notes
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