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

HRID 480074Notes

Reaction equation

HRID 480074 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-68e6644c97174533a932adf574bfc742
Source dataset
uspto-grants-2003_11
Patent number
US06649634B2

Reaction notes

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