p-Toluenesulfonic acid monohydrate → HCID 86757291, compound

HRID 651783Notes

Reaction equation

HRID 651783 reaction equation
O1CCCCC1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:22]([NH:24][N:25]1[C:30](=[O:31])[CH2:29][NH:28][CH2:27][C:26]1=[O:32])=[O:23])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].O.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44]([OH:47])(=[O:46])=[O:45])=[CH:40][CH:39]=1>C(O)(C)C.CO>[C:38]1([CH3:48])[CH:39]=[CH:40][C:41]([S:44]([OH:47])(=[O:45])=[O:46])=[CH:42][CH:43]=1.[OH:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:22]([NH:24][N:25]1[C:26](=[O:32])[CH2:27][NH:28][CH2:29][C:30]1=[O:31])=[O:23])[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:10]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86757293HCID 86757293, compound

Product 1

HCID 86757291HCID 86757291, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 0.072 g of 2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenylbutyl]-4-methyl-N-(2,6-dioxo-1-piperazinyl)valeramide in a mixture of 5 ml of isopropyl alcohol and 1 ml of methanol was treated with 0.030 g of p-toluenesulphonic acid monohydrate at 0° C. The mixture was left to warm to room temperature and was stirred overnight. Evaporation and trituration of the residue with diethyl ether gave 0.059 g of 2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-N-(2,6-dioxo-1-piperazinyl)valeramide p-toluenesulphonate in the form of an off-white solid.

Workup

  1. waitThe mixture was left
  2. customEvaporation and trituration of the residue with diethyl ether

Sources & evidence

ORD record
ord-a433d2044beb4f8894b861fc140fa71c
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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