Triethylamine → (S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid chloride

HRID 2216988Notes

Reaction equation

HRID 2216988 reaction equation
[C:1]([Si:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:6][CH2:7][C@H:8]([CH3:12])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:32]C(OCC)=O>ClCCl>[C:1]([Si:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:6][CH2:7][C@H:8]([CH3:12])[C:9]([Cl:32])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10665033(S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid

Product 1

HCID 87716621(S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-(+)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methylpropionic acid (0.44 g; 1.20 mmol) (from Example 13a supra) was dissolved in dichloromethane (3 mL, dried over molecular sieves). Triethylamine (0.36 mL; 2.58 mmol) (Aldrich) was added and the solution was cooled in an ice-water bath. Ethyl chloroformate (0.16 mL; 1.63 mmol) (Aldrich) was added dropwise and the mixture was stirred in the cold for 1 hour. The mixture was then diluted with additional dichloromethane, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to yield (S)-(+)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylpropionic acid chloride.

Workup

  1. temperaturethe solution was cooled in an ice-water bath
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cecd362cac3045ada0a1245d616d227f
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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