p-Toluenesulfonic acid → HCID 86756732, compound

HRID 1978069Notes

Reaction equation

HRID 1978069 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([CH:11]([C@@H:21]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:22]([NH:24][N:25]([S:32]([CH3:35])(=[O:34])=[O:33])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[OH:7][NH:8][C:9]([CH:11]([C@@H:21]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:22]([NH:24][N:25]([S:32]([CH3:35])(=[O:34])=[O:33])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:10]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756733HCID 86756733, compound

Product 1

HCID 86756732HCID 86756732, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.21 g of (E)-2(R)-[1(RS)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-(3-pyridyl)-3-butenyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in 5 ml of methanol was treated with 0.097 g of 4-toluenesulphonic acid. The mixture was stirred for 2.5 hours at room temperature and then diluted with water. The solid was filtered off, washed with water and diethyl ether and dried in vacuum to yield 0.138 g of (E)-2(R)-[1(RS)-(hydroxycarbamoyl)-4-(3-pyridyl)-3-butenyl]-2′-(methanesulphonyl)-4-methyl-2′-phenylvalerohydrazide in the form of a white solid.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with water and diethyl ether
  3. customdried in vacuum

Sources & evidence

ORD record
ord-529da4a4a69943248bfb66a5862313d3
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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