1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-Chloro-phenyl)-3-methoxy-N-[2-oxo-2-(2-phenyl-pyrrolidin-1-yl)-ethyl]-benzene sulfonamide

HRID 2079606노트

반응식

HRID 2079606 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:20][C:21](O)=[O:22])[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:54]1([CH:60]2[CH2:64][CH2:63][CH2:62][NH:61]2)[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:20][C:21](=[O:22])[N:61]2[CH2:62][CH2:63][CH2:64][CH:60]2[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)(=[O:10])=[O:11])=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2618922-PhenylpyrrolidineHCID 57788180[(4-Chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid

생성물 1

HCID 44197669N-(4-Chloro-phenyl)-3-methoxy-N-[2-oxo-2-(2-phenyl-pyrrolidin-1-yl)-ethyl]-benzene sulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
25 °C

실험 절차

To a solution of [(4-chlorophenyl)-(3-methoxy-benzenesulfonyl)-amino]-acetic acid (250 mg, 0.7 mmol) in dry dichloromethane (20 mL) were sequentially added EDCI (202 mg, 1.05 mmol), HOBT (142.4 mg, 1.05 mmol), and DIPEA (0.23 mL, 1.40 mmol). The reaction mixture was allowed to stir for 30 minutes under nitrogen at 25° C. 2-Phenyl-pyrrolidine (104 mg, 0.7 mmol) was added and the mixture was stirred at 25° C. for 12 h. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and water. The organic layer was dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by column chromatography over silica gel (30-40% ethyl acetate/hexane) to yield the title compound.

후처리

  1. stirringthe mixture was stirred at 25° C. for 12 h
  2. washwashed with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel (30-40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-45eec1ad653542c1b3d0b342572f17f0
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932269B2

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