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

HRID 1760948Notes

Reaction equation

HRID 1760948 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-7548f43d45c44d9eb1753f7b6da6b239
Source dataset
uspto-grants-2005_01
Patent number
US06846820B2

Reaction notes

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