Triethylamine → 6-(4-(2-(2,4,6-Trimethylbenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)hex-5-enoic acid

HRID 22131

반응식

HRID 22131 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]C)=[O:16])=[CH:6][CH:5]=1.[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:27]=1[S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C>ClCCl>[CH3:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:27]=1[S:34]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)(=[O:35])=[O:36]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 130462-Mesitylenesulfonyl chlorideHCID 54161160Methyl 6-(4-(2-aminoethyl)phenyl)-6-(3-pyridyl)hex-5-enoate

생성물 1

HCID 543168266-(4-(2-(2,4,6-Trimethylbenzenesulphonylamino)ethyl)phenyl)-6-(3-pyridyl)hex-5-enoic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 3.24 g of methyl 6-(4-(2-aminoethyl)phenyl)-6-(3-pyridyl)hex-5-enoate, 2.2 g of 2,4,6-trimethylbenzenesulphonic acid chloride and 100 ml of triethylamine in 50 ml of dichloromethane is stirred for 30 minutes at ambient temperature. Then the reaction mixture is washed twice with water, dried and evaporated down. The residue is purified over a silica gel column using ethyl acetate. The crude product obtain is heated in a mixture of 32 ml of ethanol and 5 ml of 4N sodium hydroxide solution for 30 minutes to 50° to 60° C. The reaction mixture is evaporated down, the residue is taken up in 50 ml of water and washed with ethyl acetate. The aqueous phase is adjusted to pH 5 by the addition of citric acid and extracted twice with ethyl acetate. The organic phase is dried, evaporated down and the residue is chromatographed over a silica gel column using ethyl acetate. The crude product is then recrystallised from ethyl acetate/diisopropyl ether.

후처리

  1. washThen the reaction mixture is washed twice with water
  2. customdried
  3. customevaporated down
  4. customThe residue is purified over a silica gel column

출처 및 근거

ORD 기록
ord-7df537ef2af54ad2b761aab6a318ec77
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426119

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