Methanol → HCID 178464523, compound

HRID 926074Notes

Reaction equation

HRID 926074 reaction equation
[CH2:1]([N:3]([C@H:47]1[CH2:52][CH2:51][C@H:50]([C:53]([O:55]C)=[O:54])[CH2:49][CH2:48]1)[S:4]([C:7]1[CH:8]=[C:9]([CH:44]=[CH:45][CH:46]=1)[C:10]([NH:12][C:13]1[S:14][C:15]2[CH2:43][CH2:42][CH2:41][CH2:40][C:16]=2[C:17]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][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:23][CH:22]=1)=[O:19])=[O:11])(=[O:6])=[O:5])[CH3:2].CO.[OH-].[Na+]>C1COCC1>[C:53]([C@H:50]1[CH2:51][CH2:52][C@H:47]([N:3]([CH2:1][CH3:2])[S:4]([C:7]2[CH:8]=[C:9]([CH:44]=[CH:45][CH:46]=2)[C:10]([NH:12][C:13]2[S:14][C:15]3[CH2:43][CH2:42][CH2:41][CH2:40][C:16]=3[C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([OH:36])=[O:35])=[CH:38][CH:39]=3)=[CH:23][CH:22]=2)=[O:19])=[O:11])(=[O:6])=[O:5])[CH2:48][CH2:49]1)([OH:55])=[O:54]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 178464525HCID 178464525, compound

Product 1

HCID 178464523HCID 178464523, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 230 mg of methyl 4-(3-{4-[({2-[(3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]sulfamoyl}benzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophen-3-yl}carbonyl)amino]phenyl}propyl)benzoate, 2 mL of methanol, and 2 mL of THF was added 2 mL of a 1 M aqueous NaOH solution, followed by stirring at 60° C. for 2 days. The reaction mixture was cooled and then concentrated under reduced pressure. The obtained residue was diluted with water and then neutralized with 1 M hydrochloric acid. To the reaction mixture was added 0.5 mL of THF and the precipitate was collected by filtration. The obtained solid was suspended in 10 mL of ethanol, and then the precipitate was collected by filtration to obtain 147 mg of 4-{3-[4-({[2-({3-[(trans-4-carboxycyclohexyl)(ethyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]propyl}benzoic acid as a beige crystal.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe obtained residue was diluted with water
  4. additionTo the reaction mixture was added 0.5 mL of THF
  5. filtrationthe precipitate was collected by filtration
  6. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b9089860cf6645478d4d307197f465cb
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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