p-Toluenesulfonic acid monohydrate → (E)-2'-(2-aminoethanesulphonyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide p-toluene-sulphonate

HRID 1386561Notes

Reaction equation

HRID 1386561 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([N:7]([CH2:36][CH:37]([CH3:39])[CH3:38])[NH:8][C:9](=[O:35])[C@@H:10]([C@@H:15]([C:25](=[O:34])[NH:26][O:27]C1CCCCO1)[CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])(=[O:6])=[O:5].O.[C:41]1([CH3:51])[CH:46]=[CH:45][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1>CO>[C:41]1([CH3:51])[CH:42]=[CH:43][C:44]([S:47]([OH:50])(=[O:48])=[O:49])=[CH:45][CH:46]=1.[NH2:1][CH2:2][CH2:3][S:4]([N:7]([CH2:36][CH:37]([CH3:39])[CH3:38])[NH:8][C:9](=[O:35])[C@@H:10]([C@@H:15]([C:25](=[O:34])[NH:26][OH:27])[CH2:16]/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][CH:12]([CH3:14])[CH3:13])(=[O:5])=[O:6]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757180(E)-2'-(2-aminoethanesulphonyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86757178(E)-2'-(2-aminoethanesulphonyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide p-toluene-sulphonateYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.25 g of (E)-2′-(2-aminoethanesulphonyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of methanol was treated with 0.1 g of p-toluene-sulphonic acid monohydrate. The mixture was stirred for 2.5 hours at room temperature and evaporated. The residue was triturated with diethyl ether, filtered off and dried to give 0.255 g of (E)-2′-(2-aminoethanesulphonyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide p-toluene-sulphonate in the form of a white solid.

Workup

  1. customevaporated
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-a2d8456be6214c50b23003aed5107656
Source dataset
uspto-grants-2001_07
Patent number
US06265446B1

Reaction notes

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