Triethylamine → (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-butyric acid methyl ester

HRID 1096167Notes

Reaction equation

HRID 1096167 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@H:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:15][O:14][C:12](=[O:13])[C@@H:11]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 16217854Methyl (S)-(-)-4-(tert-butyldimethylsilyloxy)-2-hydroxybutanoate

Product 1

HCID 86638104(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methanesulfonyloxy-butyric acid methyl esterYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.48 g (10.00 mmol) of methyl (S)-4-(tert-butyldimethylsilyloxy)-2-hydroxybutanoate (J. Am. Chem. Soc. 2005 127, 1090-1091) in 50 ml of CH2Cl2 was treated with 2.09 ml (15.00 mmol, 1.5 eq) of triethylamine and at 0° C. during 5 min with 0.82 ml (10.50 mmol, 1.051 eq) of methanesulfonyl chloride. After 1 h at 0° C. the reaction was partitioned between 10% aq KH2PO4/Et2O (×3), the organic phases were washed with sat. aq. NaHCO3 solution (freshly prepared) and 10% aq. NaCl solution, dried over Na2SO4 and evaporated to give 2.91 g (89%) of the title compound as yellow oil. MS: 327.1 (MH+).

Workup

  1. customAfter 1 h at 0° C. the reaction was partitioned between 10% aq KH2PO4/Et2O (×3)
  2. washthe organic phases were washed with sat. aq. NaHCO3 solution (
  3. customfreshly prepared) and 10% aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-635dbd1093c14e1daf9868942734c81f
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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