Trifluoroacetic acid → (S)-2-Amino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butan-1-ol

HRID 1455588ノート

反応式

HRID 1455588 の反応式
C(OC(=O)[NH:7][C@H:8]([CH:11]([OH:28])[C:12]1[O:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=2)=[N:15][N:16]=1)[CH2:9][CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH:8]([CH2:9][CH3:10])[C@@H:11]([C:12]1[O:13][C:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([F:25])([F:27])[F:26])=[CH:21][CH:22]=2)=[N:15][N:16]=1)[OH:28]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 57535328((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester

生成物 1

HCID 68823850(S)-2-Amino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butan-1-ol収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

((S)-1-{hydroxy-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-methyl}-propyl)-carbamic acid tert-butyl ester (0.54 mmol, 0.225 g) is dissolved in dichloromethane (9 mL) and treated with trifluoroacetic acid (1 mL). The reaction mixture is stirred for four hours. The solvents are evaporated under reduced pressure. The residue is re-dissolved in dichloromethane (20 mL) and Silicycle Triamine (5.4 mmol, 1.47 g) is added. The reaction mixture is stirred for 60 h (over the weekend). The reaction mixtures are filtered under suction and the solvents evaporated to give (S)-2-Amino-1-[5-(4-trifluoromethoxy-phenyl)-1,3,4-oxadiazol-2-yl]-butan-1-ol (0.164 g, 96%). MS: m/z=318 (M+H+)

後処理

  1. customThe solvents are evaporated under reduced pressure
  2. dissolutionThe residue is re-dissolved in dichloromethane (20 mL)
  3. stirringThe reaction mixture is stirred for 60 h (over the weekend)
  4. customThe reaction mixtures
  5. filtrationare filtered under suction
  6. customthe solvents evaporated

出典と根拠

ORDレコード
ord-9ebffeec6a3544c2b76d1a905ba2af14
出典データセット
uspto-grants-2009_01
特許番号
US07482448B2

反応ノート

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