Sodium Hydroxide → HCID 178464522, 화합물

HRID 926054

반응식

HRID 926054 반응식
[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]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 178464524HCID 178464524, 화합물

생성물 1

HCID 178464522HCID 178464522, 화합물수율 70.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ec0ed599e3143bbb2513f35b63e2a40
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284295B2

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