Acetic Acid → tert-Butyl (S)-1-(5-(3-hydroxy-4-aminophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 2075338ノート

反応式

HRID 2075338 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:11]2[S:15][C:14]([N:16]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:17][C@@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O)(=O)C>CO.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([C:11]2[S:15][C:14]([N:16]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:17][C@@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:19][C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:24][CH:25]=3)=[N:13][N:12]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 57991949tert-Butyl (S)-1-(5-(3-hydroxy-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

生成物 1

HCID 57991851tert-Butyl (S)-1-(5-(3-hydroxy-4-aminophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate収率 53%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

tert-Butyl (S)-1-(5-(3-hydroxy-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (400 mg, 625 μmol) was dissolved in 100 mL MeOH in a 500 mL round bottom flask. To this flask was added 10% Pd/C (100 mg pre-wet with water) and 1.5 mL acetic acid. The mixture was stirred under an atmosphere of hydrogen under balloon pressure for 2 hours. After filtration through a pad of celite, the solution was evaporated to dryness. The residue was re-dissolved in 150 mL EtOAc. The solution was washed with saturated ammonia chloride twice and dried over sodium sulfate. After removing the solvent, the remaining residue was subjected to silica gel column chromatograph separation using 20% to 40% EtOAc in hexane as the eluant. After removing the solvent, the desired product (200 mg, 53%) was obtained as a tan solid. LCMS (API-ES) m/z (%): 610.0 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 1.21 (s, 9H) 1.55 (s, 9H) 2.80-2.95 (m, 1H) 2.95-3.06 (m, 1H) 4.00-4.25 (m, 1H) 4.25-4.57 (m, 2H) 6.77 (d, J=8.22 Hz, 1H) 7.18 (dd, J=8.02, 1.96 Hz, 1H) 7.25 (d, J=1.76 Hz, 1H) 7.44-7.53 (m, 2H) 7.60 (d, J=8.02 Hz, 2H).

後処理

  1. filtrationAfter filtration through a pad of celite
  2. customthe solution was evaporated to dryness
  3. dissolutionThe residue was re-dissolved in 150 mL EtOAc
  4. washThe solution was washed with saturated ammonia chloride twice
  5. dry with materialdried over sodium sulfate
  6. customAfter removing the solvent
  7. customthe remaining residue was subjected to silica gel column chromatograph separation
  8. customAfter removing the solvent

出典と根拠

ORDレコード
ord-8ab0820be19f4451ab40a1b18b105db7
出典データセット
uspto-grants-2011_04
特許番号
US07919504B2

反応ノート

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