Chlorotrimethylsilane → 3-Trimethylsilyl-L-alanine methyl ester hydrochloride
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture is warmed to RT overnight
- customThe volatile components are removed on a Rotavapor and subsequently under high vacuum
- 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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