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

HRID 656615Notes

Reaction equation

HRID 656615 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 (S)-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 dichlormethane 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 (S)-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 dichlormethane
  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-489886fa2e4b416eb0f3dd0df1198fed
Source dataset
uspto-grants-2011_12
Patent number
US08071766B2

Reaction notes

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