Water → Benzyl 4-[2-(4-hydroxybenzenesulfonylamino)-1-methoxycarbonylethyl]piperazine-1-carboxylate

HRID 472130노트

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HRID 472130 반응식
C(N(CC)CC)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl.Cl.[NH2:21][CH2:22][CH:23]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:30][CH2:29]1)[C:24]([O:26][CH3:27])=[O:25].O>ClCCl>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:21][CH2:22][CH:23]([N:28]2[CH2:29][CH2:30][N:31]([C:34]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])[CH2:32][CH2:33]2)[C:24]([O:26][CH3:27])=[O:25])(=[O:17])=[O:16])=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 114240934-Hydroxybenzene-1-sulfonyl chlorideHCID 86675018Benzyl 4-(2-amino-1-methoxycarbonylethyl)piperazine-1-carboxylate dihydrochloride

생성물 1

HCID 71115508Benzyl 4-[2-(4-hydroxybenzenesulfonylamino)-1-methoxycarbonylethyl]piperazine-1-carboxylate수율 46%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

2.1 ml (15 mmol) of triethylamine and then 920 mg (5 mmol) of 4-hydroxybenzenesulfonyl chloride in 20 ml of dichloromethane are added dropwise to a solution of 1.1 g (3 mmol) of benzyl 4-(2-amino-1-methoxycarbonylethyl)piperazine-1-carboxylate dihydrochloride in 30 ml of dichloromethane, cooled beforehand to 0° C. The reaction medium is then stirred at ambient temperature for 18 h. After the addition of water, the reaction medium is extracted with dichloromethane. The organic phase is with water and then dried over magnesium sulfate, filtered and concentrated under vacuum. The crude residue obtained is purified by chromatography on silica gel, elution being carried out with a 50/50 heptane/ethyl acetate mixture. 60 mg (46%) of benzyl 4-[2-(4-hydroxybenzenesulfonylamino)-1-methoxycarbonylethyl]piperazine-1-carboxylate are obtained in the form of a white solid.

후처리

  1. extractionthe reaction medium is extracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe crude residue obtained
  6. customis purified by chromatography on silica gel, elution

출처 및 근거

ORD 기록
ord-a51e65ad6e41475e9c74590687cc6ec2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633196B2

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