p-Toluenesulfonic acid monohydrate → HCID 86757186, compound

HRID 1386565Notes

Reaction equation

HRID 1386565 reaction equation
[CH3:1][N:2]([CH3:42])[CH2:3][CH2:4][CH2:5][S:6]([N:9]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:10][C:11](=[O:37])[C@@H:12]([C@@H:17]([C:27](=[O:36])[NH:28][O:29]C1CCCCO1)[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:13][CH:14]([CH3:16])[CH3:15])(=[O:8])=[O:7].O.[C:44]1([CH3:54])[CH:49]=[CH:48][C:47]([S:50]([OH:53])(=[O:52])=[O:51])=[CH:46][CH:45]=1>CO>[C:44]1([CH3:54])[CH:45]=[CH:46][C:47]([S:50]([OH:53])(=[O:51])=[O:52])=[CH:48][CH:49]=1.[CH3:42][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][S:6]([N:9]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:10][C:11](=[O:37])[C@@H:12]([C@@H:17]([C:27](=[O:36])[NH:28][OH:29])[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:13][CH:14]([CH3:15])[CH3:16])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757188HCID 86757188, compound

Product 1

HCID 86757186HCID 86757186, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.184 g of (E)-2′-[3-(dimethylamino)propylsulphonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 4 ml of methanol was treated with 0.069 g of p-toluene-sulphonic acid monohydrate. The mixture was stirred for 3.5 hours at room temperature and evaporated. Trituration of the residue with diethyl ether gave 0.19 g of (E)-2′-[3-(dimethylamino)propylsulphonyl]-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide p-toluenesulphonate in the form of an off-white solid.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-5e16af90cb17451091c155e53e7f12de
Source dataset
uspto-grants-2001_07
Patent number
US06265446B1

Reaction notes

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