Sodium Hydroxide → HCID 178464522, compound

HRID 926054Notes

Reaction equation

HRID 926054 reaction equation
[CH2:1]([N:3]([C@H:46]1[CH2:51][CH2:50][C@H:49]([C:52]([O:54]C)=[O:53])[CH2:48][CH2:47]1)[S:4]([C:7]1[CH:8]=[C:9]([CH:43]=[CH:44][CH:45]=1)[C:10]([NH:12][C:13]1[S:14][C:15]2[CH2:42][CH2:41][CH2:40][CH2:39][C:16]=2[C:17]=1[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35]C)=[O:34])=[CH:31][CH:30]=2)=[CH:23][CH:22]=1)=[O:19])=[O:11])(=[O:6])=[O:5])[CH3:2].[OH-].[Na+]>C(O)C>[C:52]([C@H:49]1[CH2:50][CH2:51][C@H:46]([N:3]([CH2:1][CH3:2])[S:4]([C:7]2[CH:8]=[C:9]([CH:43]=[CH:44][CH:45]=2)[C:10]([NH:12][C:13]2[S:14][C:15]3[CH2:42][CH2:41][CH2:40][CH2:39][C:16]=3[C:17]=2[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([C:33]([OH:35])=[O:34])=[CH:37][CH:38]=3)=[CH:23][CH:22]=2)=[O:19])=[O:11])(=[O:6])=[O:5])[CH2:47][CH2:48]1)([OH:54])=[O:53]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178464524HCID 178464524, compound

Product 1

HCID 178464522HCID 178464522, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 300 mg of methyl 4-(2-{4-[({2-[(3-{ethyl[trans-4-(methoxycarbonyl)cyclohexyl]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 3.0 mL of ethanol was heated and refluxed overnight. The reaction mixture was concentrated under reduced pressure, and then to the obtained residue were added water, 300 mg of citric acid, and dichloromethane in this order, and the precipitate was collected by filtration. For the filtrate, the organic layer was separated and evaporated under reduced pressure. The firstly collected solid and the concentrate of the filtrate were mixed and the mixture was purified by silica gel column chromatography (chloroform-methanol). The crude product was washed with diethyl ether to obtain 203 mg of 4-{2-[4-({[2-({3-[(trans-4-carboxycyclohexyl)(ethyl)sulfamoyl]benzoyl}amino)-4,5,6,7-tetrahydro-1-benzothiophen-3-yl]carbonyl}amino)phenyl]ethyl}benzoic acid as a pale yellow crystal.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the obtained residue were added water, 300 mg of citric acid, and dichloromethane in this order
  5. filtrationthe precipitate was collected by filtration
  6. customFor the filtrate, the organic layer was separated
  7. customevaporated under reduced pressure
  8. concentrationThe firstly collected solid and the concentrate of the filtrate
  9. additionwere mixed
  10. customthe mixture was purified by silica gel column chromatography (chloroform-methanol)
  11. washThe crude product was washed with diethyl ether

Sources & evidence

ORD record
ord-1ec0ed599e3143bbb2513f35b63e2a40
Source dataset
uspto-grants-2016_03
Patent number
US09284295B2

Reaction notes

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