Cesium fluoride → (S)-Ethyl (S-phenylsulfonimidoyl)acetate

HRID 391568Notes

Reaction equation

HRID 391568 reaction equation
[C:1]1([S@@:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[N:9][Si](C)(C)C)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[Cs+]>CO.O>[C:1]1([S@@:7]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[NH:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 57657878(S)-Ethyl [S-phenyl-N-(trimethylsilyl)sulfonimidoyl]acetate2×

Product 1

HCID 57657864(S)-Ethyl (S-phenylsulfonimidoyl)acetateYield 39%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A solution of Ethyl [S-phenyl-N-(trimethylsilypsulfonimidoyl]acetate (18.7 mmol, obtained as crude oil from step 2) in MeOH—H2O (10:1, 7.5 mL) was treated with cesium fluoride (0.25 g, 1.65 mmol) in one portion. The reaction mixture was heated to 50° C. and stirred for 2 hours. The reaction mixture was concentrated, the residue absorbed to silica gel and purified by chromatography (silica gel, EtOAc-Hexane, Et3N 0.1%). The product containing fractions were concentrated to give the title compound as a pale yellow oil (1.65 g, 39% for steps 1-3).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue absorbed to silica gel
  3. custompurified by chromatography (silica gel, EtOAc-Hexane, Et3N 0.1%)
  4. additionThe product containing fractions
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-160b832a49f747d78f704d4183af5d46
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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