Triethylamine → (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate

HRID 1917514Notes

Reaction equation

HRID 1917514 reaction equation
[Si:1]([O:8][C@@H:9]([CH2:14][CH2:15]O)[C:10]([O:12][CH3:13])=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>ClCCl.CN(C1C=CN=CC=1)C>[Si:1]([O:8][C@@H:9]([CH2:14][CH2:15][S:24]([CH3:27])(=[O:26])=[O:25])[C:10]([O:12][CH3:13])=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11107713(S)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate

Product 1

HCID 86636767(S)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate (91c, 3.9 g, 15.7 mmol) in anhydrous dichloromethane was added triethylamine, DMAP, and mesyl chloride. The reaction was allowed to stir for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous phase was extracted with dicholormethane and the combine organic phases were washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent removed in vacuo to yield (5)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate (91d, 4.9 g, 15 mmol) as a yellow oil. [M+H] calc'd for C12H26O6SSi, 327; found, 327.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionThe aqueous phase was extracted with dicholormethane
  3. washthe combine organic phases were washed with brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d235bf962c7f48a984550708a9c89077
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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