p-Toluenesulfonic acid → HCID 86756896, compound

HRID 1979203Notes

Reaction equation

HRID 1979203 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:22]([NH:24][N:25]([C:30](=[O:34])[C@H:31]([OH:33])[CH3:32])[CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:22]([NH:24][N:25]([C:30](=[O:34])[C@H:31]([OH:33])[CH3:32])[CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756897HCID 86756897, compound

Product 1

HCID 86756896HCID 86756896, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.12 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(2(R)-hydroxypropionyl)-2′-isobutyl-4-methylvalerohydrazide in 20 ml of methanol was treated with 0.212 g of p-toluenesulphonic acid. The mixture was stirred for 0.5 hour at room temperature and evaporated to give a foam. This foam in ethyl acetate was washed with 5% sodium hydrogen carbonate solution and water, dried over anhydrous magnesium sulphate and evaporated to low volume. The solid which separated was washed with cold ethyl acetate and dried to give 1.584 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-(2(R)-hydroxypropionyl)-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customevaporated
  2. customto give a foam
  3. washThis foam in ethyl acetate was washed with 5% sodium hydrogen carbonate solution and water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated to low volume
  6. customThe solid which separated
  7. washwas washed with cold ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-bdc76110ae0641909285774b352b229c
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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