Sodium Hydroxide → 4-{2-[4-({[2-({3-[(2,3-Dihydroxypropyl)(methyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoic acid

HRID 1025468Notes

Reaction equation

HRID 1025468 reaction equation
[OH:1][CH:2]([CH2:48][OH:49])[CH2:3][N:4]([CH3:47])[S:5]([C:8]1[CH:9]=[C:10]([CH:44]=[CH:45][CH:46]=1)[C:11]([NH:13][C:14]1[S:15][C:16]2[CH2:43][CH2:42][CH2:41][CH2:40][C:17]=2[C:18]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36]C)=[O:35])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)=[O:20])=[O:12])(=[O:7])=[O:6].[OH-].[Na+]>C(O)C>[OH:1][CH:2]([CH2:48][OH:49])[CH2:3][N:4]([CH3:47])[S:5]([C:8]1[CH:9]=[C:10]([CH:44]=[CH:45][CH:46]=1)[C:11]([NH:13][C:14]1[S:15][C:16]2[CH2:43][CH2:42][CH2:41][CH2:40][C:17]=2[C:18]=1[C:19]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:38][CH:39]=2)=[CH:26][CH:27]=1)=[O:20])=[O:12])(=[O:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71238626Methyl 4-{2-[4-({[2-({3-[(2,3-dihydroxypropyl)(methyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate

Product 1

HCID 712385754-{2-[4-({[2-({3-[(2,3-Dihydroxypropyl)(methyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoic acidYield 79.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 230 mg of methyl 4-{2-[4-({[2-({3-[(2,3-dihydroxypropyl)(methyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoate, 1.5 mL of a 1.0 M aqueous sodium hydroxide solution, and 2.3 mL of ethanol was heated and refluxed overnight. The reaction mixture was concentrated under reduced pressure, and to the residue were added water, citric acid, and dichloromethane in this order. The organic layer was separated and concentrated under reduced pressure. The obtained residue was solidified with THF-hexane to obtain 180 mg of 4-{2-[4-({[2-({3-[(2,3-dihydroxypropyl)(methyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoic acid as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the residue were added water, citric acid, and dichloromethane in this order
  5. customThe organic layer was separated
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0451a1fa9ab342da93ba5c8f71a40739
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

Loading…