(Diethylamino)sulfur trifluoride → 4,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-butyric Acid

HRID 23757노트

반응식

HRID 23757 반응식
C(O[C:4](=O)[C:5]([F:21])([F:20])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)C.C(N(S(F)(F)F)CC)C.C([O:34][C:35](=[O:52])[C:36](C1C=CC(C2C=CC(OC)=CC=2)=CC=1)=O)C>ClCCl>[F:21][C:5]([F:20])([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[CH:10][CH:11]=1)[CH2:4][CH2:36][C:35]([OH:52])=[O:34]

참가 물질

5

반응물 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 46220012(4'-Methoxybiphenyl-4-yl)difluoroacetic acid ethyl esterHCID 69784836(4'-Methoxy-biphenyl-4-yl)-oxo-acetic acid ethyl ester

생성물 1

HCID 98395084,4-Difluoro-4-(4'-methoxy-biphenyl-4-yl)-butyric Acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Difluoro-(4′-methoxy-biphenyl-4-yl)-acetic acid ethyl ester. Diethylaminosulfur trifluoride (5 mL) is added directly to (4′-methoxy-biphenyl-4-yl)-oxo-acetic acid ethyl ester (3.77 g, 13.3 mmol), prepared as described by Neidlin, et. al., Arzneim.-Forsch. 1983, 33, 691-3. Dichloromethane (2 mL) is added and the mixture is stirred overnight at room temperature. The reaction is diluted with dichloromethane and slowly added to ice water. This mixture is extracted with ethyl acetate twice. The combined organic extracts are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes) to give the desired product as a pale yellow solid.

후처리

  1. customprepared
  2. extractionThis mixture is extracted with ethyl acetate twice
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-e8ca589573444b1b96f7b6fcfff3247d
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852751B2

반응 노트

불러오는 중…