p-Toluenesulfonic acid → HCID 86756891, compound

HRID 1979201Notes

Reaction equation

HRID 1979201 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:22]([NH:24][N:25]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:26](=[O:31])[C@@H:27]([CH2:29][OH:30])[NH2:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].[C:40]1([CH3:50])[CH:45]=[CH:44][C:43]([S:46]([OH:49])(=[O:48])=[O:47])=[CH:42][CH:41]=1>CO>[C:40]1([CH3:50])[CH:41]=[CH:42][C:43]([S:46]([OH:49])(=[O:47])=[O:48])=[CH:44][CH:45]=1.[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:22]([NH:24][N:25]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:26](=[O:31])[C@@H:27]([CH2:29][OH:30])[NH2:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86756893HCID 86756893, compound

Product 1

HCID 86756891HCID 86756891, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.175 g (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(D-seryl)valerohydrazide in 2 ml of methanol was treated with 0.073 g of p-toluenesulphonic acid. The mixture was stirred for 3 hours at room temperature and evaporated. The residue was triturated with diethyl ether, filtered off and dried to give 0.160 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(D-seryl)valerohydrazide p-toluenesulphonate 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-87ac12092c6a452da506f471aa676062
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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