Sodium hydride → 5-Benzoylthio-2-methyl-2-(p-nitrobenzyloxycarbonyl)aminopentane

HRID 1252227Notes

Reaction equation

HRID 1252227 reaction equation
[C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C1(C)C=CC(S(O[CH2:22][CH2:23][CH2:24][C:25]([CH3:41])([NH:27][C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=2)=[O:29])[CH3:26])(=O)=O)=CC=1>CN(C)C=O.C(OCC)(=O)C>[C:1]([S:8][CH2:22][CH2:23][CH2:24][C:25]([CH3:41])([NH:27][C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=1)=[O:29])[CH3:26])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 201407755-p-Toluenesulfonyloxy-2-methyl-2-(p-nitrobenzyloxycarbonyl)aminopentaneHCID 178526132HCID 178526132, compound

Product 1

HCID 201407765-Benzoylthio-2-methyl-2-(p-nitrobenzyloxycarbonyl)aminopentane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of thiobenzoic acid (890 mg) and sodium hydride (50%) (220 mg) in dimethylformamide (8 ml) was stirred for 10 minutes with ice-cooling. 5-p-Toluenesulfonyloxy-2-methyl-2-(p-nitrobenzyloxycarbonyl)aminopentane (1.64 g) in dimethylformamide (8 ml) was added thereto, followed by stirring for 25 minutes. The reaction mixture was diluted with ethyl acetate, washed with dilute hydrochloric acid and then water, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 5-benzoylthio-2-methyl-2-(p-nitrobenzyloxycarbonyl)aminopentane.

Workup

  1. temperaturecooling
  2. stirringby stirring for 25 minutes
  3. washwashed with dilute hydrochloric acid
  4. dry with materialwater, dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give an oily residue which
  7. customwas then purified by silica gel chromatography

Sources & evidence

ORD record
ord-5d36794649ab4b0999f1d0aed3840bbb
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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