p-Toluenesulfonic acid → HCID 86756888, compound

HRID 1979199Notes

Reaction equation

HRID 1979199 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])[CH: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])[CH: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 86756889HCID 86756889, compound

Product 1

HCID 86756888HCID 86756888, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.71 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(2(RS)-hydroxypropionyl)-2′-isobutyl-4-methylvalerohydrazide in 8 ml of methanol was treated with 0.071 g of p-toluenesulphonic acid. The mixture was stirred for 1 hour at room temperature and evaporated to give a foam. This foam was triturated with diethyl ether, filtered off and dried to give 0.425 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-(2(RS)-hydroxypropionyl)-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customevaporated
  2. customto give a foam
  3. customThis foam was triturated with diethyl ether
  4. filtrationfiltered off
  5. customdried

Sources & evidence

ORD record
ord-e4055027d0044b058c98f4321de5a48d
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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