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

HRID 1455588노트

반응식

HRID 1455588 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

((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+)

후처리

  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

출처 및 근거

ORD 기록
ord-9ebffeec6a3544c2b76d1a905ba2af14
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482448B2

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