p-Toluenesulfonic acid monohydrate → HCID 86756963, compound

HRID 1979254Notes

Reaction equation

HRID 1979254 reaction equation
[NH2:1][C@@H:2]([C:4]([N:6]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:7][C:8](=[O:33])[C@@H:9]([CH:14]([C:23](=[O:32])[NH:24][O:25]C1CCCCO1)[CH2:15]/[CH:16]=[CH:17]/[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:5])[CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[NH2:1][C@@H:2]([C:4]([N:6]([CH2:34][CH:35]([CH3:37])[CH3:36])[NH:7][C:8](=[O:33])[C@@H:9]([CH:14]([C:23](=[O:32])[NH:24][OH:25])[CH2:15]/[CH:16]=[CH:17]/[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:5])[CH3:3]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86756964HCID 86756964, compound

Product 1

HCID 86756963HCID 86756963, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.180 g of (E)-2′-(D-alanyl)-2(R)-[1(RS)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-(2-thienyl)-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of methanol was treated with 0.077 g of p-toluenesulphonic acid monohydrate. The mixture was stirred at room temperature for 2 hours and evaporated. The residue was purified by column chromatography on silica gel, using dichloromethane/methanol (95:5) for the elution, to give 0.056 g of (E)-2′-(D-alanyl)-2(R)-[1(RS)-(hydroxycarbamoyl)-4-(2-thienyl)-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in the form of an off-white solid.

Workup

  1. customevaporated
  2. customThe residue was purified by column chromatography on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-1db6ff22945c4eefab55da0c6f3315b0
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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