p-Toluenesulfonic acid → (E)-2'-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide p-toluenesulphonate

HRID 1979190Notes

Reaction equation

HRID 1979190 reaction equation
[NH2:1][C:2]1([C:7]([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]C2CCCCO2)[CH2:18]/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:42]1([CH3:52])[CH:47]=[CH:46][C:45]([S:48]([OH:51])(=[O:50])=[O:49])=[CH:44][CH:43]=1>CO>[C:42]1([CH3:52])[CH:43]=[CH:44][C:45]([S:48]([OH:51])(=[O:49])=[O:50])=[CH:46][CH:47]=1.[NH2:1][C:2]1([C:7]([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]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:8])[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756877(E)-2'-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide

Product 1

HCID 86756875(E)-2'-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2'-isobutyl-4-methylvalerohydrazide p-toluenesulphonateYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.35 g of (E)-2′-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 3 ml of methanol was treated with 0.14 g of p-toluenesulphonic acid. The mixture was stirred for 1.7 hours at room temperature and evaporated to give a foam. This foam was triturated with diethyl ether, filtered off and dried to give 0.32 g of (E)-2′-[(1-amino-1-cyclopentyl)carbonyl]-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide p-toluenesulphonate 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-741a6ff9dc6247ee8c6ea4f2b957a445
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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