4-Fluorophenol → (S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid

HRID 983491

반응식

HRID 983491 반응식
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][SH:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[CH3:16]SC#N.[Cl-].[Al+3].[Cl-].[Cl-].B(Cl)(Cl)Cl>C(Cl)CCl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16]2[S:4][CH2:3][C@H:2]([C:5]([OH:7])=[O:6])[N:1]=2)[CH:10]=1

참가 물질

7

반응물 5

HCID 97324-FluorophenolHCID 11168Methyl thiocyanateHCID 25135Boron TrichlorideHCID 92851D-CysteineHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 136411678(S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

(S)-4,5-Dihydro-2-(5-fluoro-2-hydroxyphenyl)-4-thiazolecarboxylic acid (5′-fluorodesazadesmethylDFT, 29a) is prepared from the cyclization of D-cysteine onto 5-fluoro-2-hydroxybenzonitrile in slightly acidic buffer. The aromatic precursor could be made by direct cyanation of p-fluorophenol using methyl thiocyanate, aluminum chloride, and boron trichloride in ethylene dichloride followed by heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990)).

후처리

  1. temperatureby heating in aqueous base (Adachi et al., Syn. Commun. 20:71-84 (1990))

출처 및 근거

ORD 기록
ord-8d305a17bda041948afaccf7ffaa9077
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06864270B2

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