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

HRID 1819670ノート

反応式

HRID 1819670 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9db34d61306b4800b8c92367317d6318
出典データセット
uspto-grants-2009_10
特許番号
US07601744B2

反応ノート

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