Methanol → HCID 19766984, compound

HRID 1591393Notes

Reaction equation

HRID 1591393 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH2:20][C:21]([NH:23][C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)=[O:22])[CH:14]=[CH:13][C:12]=2[CH2:11]1)(=[O:8])=[O:7].CO.[OH-].[Na+]>O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][CH:10]1[CH2:19][CH2:18][C:17]2[CH:16]=[C:15]([CH2:20][C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:32][CH:33]=3)=[O:22])[CH:14]=[CH:13][C:12]=2[CH2:11]1)(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19766982HCID 19766982, compound

Product 1

HCID 19766984HCID 19766984, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.45 g of methyl 4-{[6-(2-thienyl)sulfonylamino-5,6,7,8-tetrahydronaphthalene-2-yl]acetylamino}benzoate, 10 ml of methanol, 9 ml of a 2N aqueous sodium hydroxide solution and 4 ml of tetrahydrofuran is stirred at room temperature overnight. Methanol and tetrahydrofuran are distilled off, and the residual mixture is washed and acidified. The precipitated crystals are collected by filtration, washed, dired and recrystallized from a mixture of tetrahydrofuran and isopropyl ether to give 1.33 g of 4-{[6-(2-thienyl)sulfonylamino-5,6,7,8-tetrahydronaphthalene-2-yl]acetylamino}benzoic acid as colorless crystals.

Workup

  1. distillationMethanol and tetrahydrofuran are distilled off
  2. washthe residual mixture is washed
  3. filtrationThe precipitated crystals are collected by filtration
  4. washwashed
  5. customdired and recrystallized from a mixture of tetrahydrofuran and isopropyl ether

Sources & evidence

ORD record
ord-0b8523d478b545bfab9d99176d5b1198
Source dataset
uspto-grants-1993_04
Patent number
US05206418

Reaction notes

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