Methanol → HCID 19766984, compound

HRID 1591410Notes

Reaction equation

HRID 1591410 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, dried 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. customdried
  6. customrecrystallized from a mixture of tetrahydrofuran and isopropyl ether

Sources & evidence

ORD record
ord-fd284d5bc8654ccb8407ffb4dd6ba3fd
Source dataset
uspto-grants-1993_04
Patent number
US05206428

Reaction notes

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