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

HRID 23757ノート

反応式

HRID 23757 の反応式
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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e8ca589573444b1b96f7b6fcfff3247d
出典データセット
uspto-grants-2005_02
特許番号
US06852751B2

反応ノート

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