Ethyl Acetate → 2-(5-Amino-2-bromophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1198695ノート

反応式

HRID 1198695 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[S:30](=[O:37])(=[O:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:20][C:19]=2[F:38])[C:13]([CH2:39][CH2:40][CH2:41][CH3:42])=[N:12]1.[OH-].[Na+].C(OCC)(=O)C>C1COCC1.Cl>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([N:11]2[C:15](=[O:16])[N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30](=[O:37])(=[O:36])[NH:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[CH:20][C:19]=3[F:38])[C:13]([CH2:39][CH2:40][CH2:41][CH3:42])=[N:12]2)[CH:4]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 103494052-(2-Bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one

生成物 1

HCID 191027882-(5-Amino-2-bromophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one収率 68.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A stirred solution of 200 mg (0.303 mmol) of 2-(2-bromo-5-nitrophenyl)-4-[[2'-(N-t-butylsulfamoyl)-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step C) in 3.5 mL of THF was cooled to 0° C. and treated dropwise with a solution of 542 mg (2.4 mmol) of stannous chloride dihydrate in 1.5 mL of concentrated hydrochloric acid. After 45 minutes, the mixture was added to a vigorously stirred mixture of 50% NaOH and ice. Ethyl acetate (15 mL) was added, and the mixture was stirred at 0° C. for 1.5 hours. The phases were separated, and the aqueous fraction was re-extracted twice with ethyl acetate. The combined organic fractions were washed with water and brine and dried over anhydrous Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed on silica gel to give 131 mg (68%) of the title compound as a stiff, off-white foam, mp 103°-105° C.; homogeneous by TLC (95:5 CH2Cl2 --MeOH); mass spectrum (FAB) m/e 629, 631 (M+1)+.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous fraction was re-extracted twice with ethyl acetate
  3. washThe combined organic fractions were washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe filtered solution was concentrated
  6. customchromatographed on silica gel

出典と根拠

ORDレコード
ord-edb8436370164420b48b4f6103cc0c8f
出典データセット
uspto-grants-1994_01
特許番号
US05281614

反応ノート

読み込み中…