Chlorotrimethylsilane → (2R,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid methyl ester Hydrochloride

HRID 379016Notes

Reaction equation

HRID 379016 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]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 638739(2R,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid

Product 1

HCID 69746370(2R,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid methyl ester Hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperatureat reflux for 5.5 hours
  2. concentrationconcentrated to a foam

Sources & evidence

ORD record
ord-1b37667def7745ad8c6182c82ede0123
Source dataset
uspto-grants-2001_10
Patent number
US06297269B1

Reaction notes

Loading…