Triphenylphosphine → 1-[(1R)-3-chloro-1-(3-chloro-5-fluorophenyl)propyl]-3-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1819670노트

반응식

HRID 1819670 반응식
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][S:5]1(=[O:14])=[O:13])([CH3:3])[CH3:2].[Cl:15][CH2:16][CH2:17][C@@H:18]([C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([Cl:27])[CH:21]=1)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:15][CH2:16][CH2:17][C@@H:18]([N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([CH:1]([CH3:3])[CH3:2])[S:5]1(=[O:13])=[O:14])[C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([Cl:27])[CH:21]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 596406791-(Propan-2-yl)-1,3-dihydro-2lambda6,1,3-benzothiadiazole-2,2-dioneHCID 68523631(1S)-3-chloro-1-(3-chloro-5-fluorophenyl)propan-1-ol

생성물 1

HCID 690592361-[(1R)-3-chloro-1-(3-chloro-5-fluorophenyl)propyl]-3-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide수율 82.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To mixture of 1-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1.28 g, 6.00 mmol), (1S)-3-chloro-1-(3-chloro-5-fluorophenyl)propan-1-ol (1.34 g, 6.00 mmol) and triphenylphosphine (1.73 g, 6.60 mmol, 1.1 equiv.) in tetrahydrofuran (20 mL) under nitrogen was added slowly diisopropyl azodicarboxylate (1.28 mL, 6.60 mmol, 1.1 equiv.) via a syringe at 0° C. The resulting solution was stirred at room temperature overnight. Solvent was removed under reduced pressure and the viscous brown liquid residue was purified using Isco CombiFlash Companion column chromatography (silica gel, 0-15% ethyl acetate/hexane) to give 2.06 g (82%) of 1-[(1R)-3-chloro-1-(3-chloro-5-fluorophenyl)propyl]-3-isopropyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide as a white solid.

후처리

  1. customSolvent was removed under reduced pressure
  2. customthe viscous brown liquid residue was purified

출처 및 근거

ORD 기록
ord-9db34d61306b4800b8c92367317d6318
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601744B2

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