p-Toluenesulfonic acid → HCID 86756730, compound

HRID 1978068Notes

Reaction equation

HRID 1978068 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]([CH3:33])[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]([CH3:32])[CH3:33])[CH2:26][CH:27]([CH3:28])[CH3:29])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756731HCID 86756731, compound

Product 1

HCID 86756730HCID 86756730, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.32 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutryl-2′-isobutyl-4-methylvalerohydrazide in 10 ml of methanol was treated with 0.03 g of 4-toluenesulphonic acid. The mixture was stirred for 2 hours at room temperature and then the solvent was evaporated to leave a glass. This residue was triturated with diethyl ether to give 0.15 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyryl-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. customthe solvent was evaporated
  2. customto leave a glass
  3. customThis residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-c9dcee4c77914b819d8649e717797eb2
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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