Sodium hydride → HCID 131715096, compound

HRID 542361Notes

Reaction equation

HRID 542361 reaction equation
[C:1]1([C:7]([SH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:23]([CH:27]([O:37][SiH:38]([CH3:40])[CH3:39])[C@@H:28]1[C@@H:31](S(C)(=O)=O)[NH:30][C:29]1=[O:36])([CH3:26])([CH3:25])[CH3:24]>CO.CC(C)=O.O>[C:23]([CH:27]([O:37][SiH:38]([CH3:40])[CH3:39])[C@@H:28]1[C@@H:31]([S:20][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:30][C:29]1=[O:36])([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 131715097HCID 131715097, compound

Product 1

HCID 131715096HCID 131715096, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

At 0°, 12.5 g of triphenylmethyl mercaptan are suspended in 70 ml of methanol and there is added in portions, over a period of 10 minutes, a total of 2.2 g of a 55% sodium hydride suspension in oil. There is then added dropwise, over a period of 30 minutes, an emulsion of 11.1 g of (3S,4R)-3-(tert.-butyldimethylsilyloxymethyl)-4-methylsulphonylazetidin-2-one (European Patent Application No. 82113) in 70 ml of acetone and 70 ml of water. After being stirred for 30 minutes at 0° and for 1 hour at room temperature, the reaction mixture is concentrated in a rotary evaporator, methylene chloride is added thereto, and the aqueous phase is separated off. The organic solution is washed with brine and dried over sodium sulphate. After concentration, the crude title compound is purified by chromatography over silica gel (eluant toluene/ethyl acetate 19:1). TLC (toluene/ethyl acetate 19:1): Rf =0.64; IR (methylene chloride): 3390, 1760, 1117, 835 cm-1.

Workup

  1. customAt 0°
  2. additionthere is added in portions, over a period of 10 minutes
  3. additionThere is then added dropwise, over a period of 30 minutes
  4. concentrationthe reaction mixture is concentrated in a rotary evaporator, methylene chloride
  5. additionis added
  6. customthe aqueous phase is separated off
  7. washThe organic solution is washed with brine
  8. dry with materialdried over sodium sulphate
  9. concentrationAfter concentration
  10. customthe crude title compound is purified by chromatography over silica gel (eluant toluene/ethyl acetate 19:1)

Sources & evidence

ORD record
ord-0de283230006412f8611e9354f845fc5
Source dataset
uspto-grants-1987_04
Patent number
US04656165

Reaction notes

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