p-Toluenesulfonic acid monohydrate → HCID 86756935, compound

HRID 1979232Notes

Reaction equation

HRID 1979232 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:22]([NH:24][N:25]([CH2:41][CH:42]([CH3:44])[CH3:43])[C:26](=[O:40])[CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])=[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]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:22]([NH:24][N:25]([CH2:41][CH:42]([CH3:43])[CH3:44])[C:26](=[O:40])[CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])=[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 86756936HCID 86756936, compound

Product 1

HCID 86756935HCID 86756935, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.050 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(3-phthalimidopropionyl)valerohydrazide in 5 ml of methanol was treated with 0.005 g of p-toluenesulphonic acid monohydrate. The mixture was stirred for 1 hr at room temperature and evaporated. The residue was triturated with diethyl ether, filtered off and dried to give 0.009 g of (E)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methyl-2′-(3-phthalimidopropionyl)valerohydrazide in the form of an off-white solid.

Workup

  1. customevaporated
  2. customThe residue was triturated with diethyl ether
  3. filtrationfiltered off
  4. customdried

Sources & evidence

ORD record
ord-547124a44f504591ab07ba39d8283143
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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