Chlorotrimethylsilane → (2R,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid methyl ester Hydrochloride
Reaction equation
[NH2:1][C@H:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C@@H:3]([OH:7])[C:4]([OH:6])=[O:5].[Cl:15][Si](C)(C)[CH3:17]>CO>[ClH:15].[CH3:17][O:5][C:4](=[O:6])[C@H:3]([OH:7])[C@H:2]([NH2:1])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of (2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid (200 mg, 1.0 mmol, Sigma Chemical Co. (St. Louis, Mo.), chlorotrimethylsilane (500 mg, 4.6 mmol) and methanol (2 mL) was heated at reflux for 5.5 hours and concentrated to a foam: Yield 244 mg, 100%.
Workup
- temperatureat reflux for 5.5 hours
- concentrationconcentrated to a foam
Sources & evidence
- ORD record
- ord-1b37667def7745ad8c6182c82ede0123
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297269B1
Reaction notes
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