p-Toluenesulfonic acid monohydrate → HCID 86756946, compound

HRID 1979238Notes

Reaction equation

HRID 1979238 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([C:30](=[O:36])[CH2:31][CH2:32][CH:33]([OH:35])[CH3:34])[CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:37][CH:38]([CH3:40])[CH3:39])[C:22]([NH:24][N:25]([C:30](=[O:36])[CH2:31][CH2:32][CH:33]([OH:35])[CH3:34])[CH2:26][CH:27]([CH3:29])[CH3:28])=[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 521998p-Toluenesulfonic acid monohydrateHCID 86756947HCID 86756947, compound

Product 1

HCID 86756946HCID 86756946, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.150 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(4(RS)-hydroxyvaleryl)-2′-isobutyl-4-methylvalerohydrazide in 5 ml of methanol was treated with 0.015 g of p-toluenesulphonic acid monohydrate. The mixture was stirred at room temperature for 2 hours and evaporated. The residue was triturated with diethyl ether, filtered off and dried to give 0.027 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-(4(RS)-hydroxyvaleryl)-2′-isobutyl-4-methylvalerohydrazide 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-79c83d9a8a0b4c59bed09fc936a6007c
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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