Reaction #40295

ord-973258b32ab84a219a5fabe31279058c

Reaction equation

CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O
compound
CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O
(2R)—N-tert-Butoxycarbonyl-3-trimethylsilylalanine
C[Si](C)(C)Cl
Trimethylsilyl chloride
→
COC(=O)[C@@H](N)C[Si](C)(C)C.Cl
(2R)-3-Trimethylsilylalanine methyl ester hydrochloride

Reactants

CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O
compound
CC(C)(C)OC(=O)N[C@@H](C[Si](C)(C)C)C(=O)O
(2R)—N-tert-Butoxycarbonyl-3-trimethylsilylalanine
C[Si](C)(C)Cl
Trimethylsilyl chloride

Reagents

None

Solvents

CO
methanol

Conditions

Temperature
0°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

The compound of Example 6A (300 mg) is dissolved in methanol (3 ml) and cooled to 0° C. Trimethylsilyl chloride (590 mg, 4.7 eq.) is added dropwise in the course of 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 (224 mg, 92% of th.) is obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727956B2uspto-grants-2010_06