Chlorotrimethylsilane → 3-Trimethylsilyl-L-alanine methyl ester hydrochloride

HRID 2237376Notes

Reaction equation

HRID 2237376 reaction equation
C(OC([NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=O)(C)(C)C.[CH3:18][Si]([Cl:22])(C)C>CO>[ClH:22].[CH3:18][O:17][C:15](=[O:16])[C@H:9]([CH2:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[NH2:8]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 57435232HCID 57435232, compound

Product 1

HCID 866191323-Trimethylsilyl-L-alanine methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The compound from example 72A (300 mg) is dissolved in methanol (3 ml) and cooled to 0° C. Trimethylsilyl chloride (590 mg, 4.7 equivalents) is added dropwise within 30 min and the mixture is warmed to RT overnight. The volatile components are removed on a Rotavapor and subsequently under high vacuum. The target compound is obtained (224 mg, 92% of theory).

Workup

  1. temperaturethe mixture is warmed to RT overnight
  2. customThe volatile components are removed on a Rotavapor and subsequently under high vacuum
  3. customThe target compound is obtained (224 mg, 92% of theory)

Sources & evidence

ORD record
ord-b680d83e63ec44aabb2ee070cd6db370
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

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