Toluene → HCID 69944313, compound

HRID 1978093Notes

Reaction equation

HRID 1978093 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:15]([O:19][C:20]([C:22]([C@@H:24]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:25]([NH:27][N:28]([CH2:33][CH:34]([CH3:36])[CH3:35])[S:29]([CH3:32])(=[O:31])=[O:30])=[O:26])=[CH2:23])=[O:21])([CH3:18])([CH3:17])[CH3:16].C1(C)C=CC=CC=1>C(OCC)(=O)C>[C:15]([O:19][C:20]([C@H:22]([C@@H:24]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:25]([NH:27][N:28]([CH2:33][CH:34]([CH3:35])[CH3:36])[S:29]([CH3:32])(=[O:31])=[O:30])=[O:26])[CH2:23][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:21])([CH3:16])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7969Thiophenol2×HCID 8471TriethylamineHCID 86756755HCID 86756755, compound

Product 1

HCID 69944313HCID 69944313, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.183 g of thiophenol and 0.356 ml of triethylamine were added to a solution of 0.500 g of 2(R)-[1(tertbutoxycarbonyl)vinyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide in 20 of toluene and stirring under a nitrogen atmosphere was continued for 48 hours. A further 0.183 ml of thiophenol was added to the mixture and stirring was continued for 48 hours at 60° C. The mixture was then cooled to room temperature and diluted with ethyl acetate. The mixture was washed in succession with 1M aqueous hyrochloric acid, 1M aqueous sodium hydroxide and brine. The organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated. Trituration with hexane gave 0.307 g of 2(R)-[1(S)-(tertbutoxycarbonyl)-2-(phenylthio)ethyl]-2′-isobutyl-2′-(methanesulphonyl)-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 48 hours at 60° C
  3. washThe mixture was washed in succession with 1M aqueous hyrochloric acid, 1M aqueous sodium hydroxide and brine
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7bd370d7873b41a788e304180f741b55
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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