p-Toluenesulfonic acid monohydrate → HCID 59166705, compound

HRID 1442681Notes

Reaction equation

HRID 1442681 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=O)[C:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:19]([CH3:31])[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[C:6]([OH:33])[CH:5]=1.S(O)(C1C=CC(C)=CC=1)(=O)=O.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:11]([C:12]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:19]([CH3:31])[CH:18]=3)([CH2:15][CH3:16])[CH2:13][CH3:14])[O:33][C:6]=2[CH:5]=1)=[O:34]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59166710HCID 59166710, compound

Product 1

HCID 59166705HCID 59166705, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 4-[2-(4-benzyloxy-3-methyl-phenyl)-2-ethyl-butyrylamino]-3-hydroxy-benzoic acid methyl ester (2.15 g, 4.66 mmol) in toluene (50 mL) is treated with TsOH—H2O (443 mg, 2.33 mmol). The reaction is heated to 160° C. for 60 m. The reaction mixture is cooled down, and toluene is removed under vacuum. The residue is purified by column chromatography (10% EtOAc/Hex) to give the title compound as an oil (1.50 g, 72%) MS (ES) m/e: 444.2 (M+1).

Workup

  1. temperatureThe reaction mixture is cooled down
  2. customtoluene is removed under vacuum
  3. customThe residue is purified by column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-208dea9acd0143008e1e69db22728ca1
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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