Potassium trimethylsilanolate → HCID 59267979, compound

HRID 1809389Notes

Reaction equation

HRID 1809389 reaction equation
C([O:3][C:4](=[O:15])[C:5]([S:8]([N:11]1[CH2:14][CH2:13][CH2:12]1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.C[Si](C)(C)[O-].[K+]>C1COCC1.Cl>[N:11]1([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:15])=[O:3])(=[O:10])=[O:9])[CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 59267897HCID 59267897, compound

Product 1

HCID 59267979HCID 59267979, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 g (21 mmol) of 2-(azetidine-1-sulfonyl)-2-methyl-propionic acid ethyl ester in THF (200 mL) at room temperature are added 8.2 g (64 mmol) of potassium trimethylsilanolate. The reaction is stirred for 1 h. The mixture is diluted with 1M aqueous HCl solution (50 mL) and extracted with DCM (250 mL). The organic phase is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to provide 4.1 g of 2-(azetidine-1-sulfonyl)-2-methyl-propionic acid as a white solid. Yield: 94%, ES-MS: m/z 208 [M+H].

Workup

  1. extractionextracted with DCM (250 mL)
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-309de3c231f04819b614a22a713af705
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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