p-Toluenesulfonic acid monohydrate → HCID 86756956, compound

HRID 1979246Notes

Reaction equation

HRID 1979246 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C@@H:21]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:22]([NH:24][N:25]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:26](=[O:35])[CH2:27][C:28]([N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[O:29])=[O:23])[C:11](=[O:20])[NH:12][O:13]C2CCCCO2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[C:45]1([CH3:55])[CH:50]=[CH:49][C:48]([S:51]([OH:54])(=[O:53])=[O:52])=[CH:47][CH:46]=1>CO>[C:45]1([CH3:55])[CH:46]=[CH:47][C:48]([S:51]([OH:54])(=[O:52])=[O:53])=[CH:49][CH:50]=1.[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C@@H:21]([CH2:40][CH:41]([CH3:43])[CH3:42])[C:22]([NH:24][N:25]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:26](=[O:35])[CH2:27][C:28]([N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)=[O:29])=[O:23])[C:11](=[O:20])[NH:12][OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86756958HCID 86756958, compound

Product 1

HCID 86756956HCID 86756956, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.205 g of 2(R)-(4-Cyclohexyl-1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]butyl]-2′-isobutyl-4-methyl-2′-[2-(1-imidazoyl)acetyl]valerohydrazide in 5 ml of methanol was treated with 0.075 g of p-toluenesulphonic acid monohydrate. The mixture was stirred at room temperature for 6 hours and evaporated. The residue was purified by flash column chromatography on silica gel using methanol/dichloromethane (5:95) as the eluant to give 0.080 g of 2(R)-[4-cyclohexyl-1(S)-(hydroxycarbamoyl)butyl]-2′-isobutyl-4-methyl-2′-(2-(1-imidazoyl)acetyl]valerohydrazide p-toluenesulphonate in the form of a white solid.

Workup

  1. customevaporated
  2. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-9cfd034dfd5c4d00b98b0ed2e7836edc
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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