Sodium Hydroxide → HCID 71238617, compound

HRID 926072Notes

Reaction equation

HRID 926072 reaction equation
[CH2:1]([N:3]([S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:55])[NH:24][C:25]2[S:26][C:27]3[CH2:54][CH2:53][CH2:52][CH2:51][C:28]=3[C:29]=2[C:30](=[O:50])[NH:31][C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][C:43]([C:46]([O:48]C)=[O:47])=[CH:42][CH:41]=3)=[CH:34][CH:33]=2)[CH:18]=1)(=[O:16])=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[CH:6][CH:5]=1)[CH3:2].[OH-].[Na+]>CO>[C:46]([C:43]1[CH:44]=[CH:45][C:40]([CH2:39][CH2:38][C:35]2[CH:34]=[CH:33][C:32]([NH:31][C:30]([C:29]3[C:28]4[CH2:51][CH2:52][CH2:53][CH2:54][C:27]=4[S:26][C:25]=3[NH:24][C:23]([C:19]3[CH:18]=[C:17]([S:14]([N:3]([CH2:1][CH3:2])[C:4]4[CH:5]=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[CH:12][CH:13]=4)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=3)=[O:55])=[O:50])=[CH:37][CH:36]=2)=[CH:41][CH:42]=1)([OH:48])=[O:47]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68207783HCID 68207783, compound

Product 1

HCID 71238617HCID 71238617, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 275 mg of methyl 4-(ethyl{[3-({3-[(4-{2-[4-(methoxycarbonyl)phenyl]ethyl}phenyl)carbamoyl]-4,5,6,7-tetrahydro-1-benzothiophen-2-yl}carbamoyl)phenyl]sulfonyl}amino)benzoate and 5.0 mL of methanol was added 2.0 mL of a 1 M aqueous sodium hydroxide solution, followed by stirring at 60° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, then to the residue was added 1 M hydrochloric acid, and the precipitate was collected by filtration. The obtained yellowish-white solid was solidified with methanol and the precipitate was collected by filtration to obtain 248 mg of 4-{[(3-{[3-({4-[2-(4-carboxyphenyl)ethyl]phenyl}carbamoyl)-4,5,6,7-tetrahydro-1-benzothiophen-2-yl]carbamoyl}phenyl)sulfonyl](ethyl)amino}benzoic acid as yellowish-white crystal.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added 1 M hydrochloric acid
  3. filtrationthe precipitate was collected by filtration
  4. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-94bb895198654f159675a29dc2ccdf28
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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