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

HRID 1765681노트

반응식

HRID 1765681 반응식
C(OC(=O)[NH:7][CH:8]([CH:11]([OH:24])[C:12](=[NH:23])[NH:13][O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH3:10])(C)(C)C.FC(F)(F)C(O)=O>COCCOCCOC.ClCCl>[NH2:7][CH:8]([CH2:9][CH3:10])[CH:11]([C:12]1[N:23]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:14][N:13]=1)[OH:24]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 178458006[(Z)-[1-amino-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentylidene]amino] benzoate

생성물 1

HCID 220540072-Amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol수율 29.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8150Diglyme용매

실험 절차

A solution of (3) (1.5 g, 4.3 mmol) in diglyme was heated at 150° C. in a microwave reactor (Smith Creator, S00219) for 40 minutes. Solvent evaporated under vacuum in Genevac Evaporator at 80° C. for 3 hours to give a brown solid. This was taken in dichloromethane (40 ml) and treated with trifluoroacetic acid at room temperature for 2 hours. Solvent evaporated to dryness under reduced pressure, crude taken in water, washed with DCM, aqueous layer basified with 1M NaOH solution and extracted with dichloromethane. Organic layer dried over Na2SO4 and evaporated under reduced pressure to give 2-amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol (300 mg) as a pale brown solid. 1HNMR (CDCl3) 8.14–8.10 (m, 2H), 7.59–7.47 (m, 3H), 4.83 & 4.65 (d, J=5 Hz, 1H), 3.18–3.05 (2m, 1H), 1.71–1.20 (m, 2H), 1.05–0.97 (2×t, J=7.2 Hz, 3H).

후처리

  1. customSolvent evaporated under vacuum in Genevac Evaporator at 80° C. for 3 hours
  2. customto give a brown solid
  3. customSolvent evaporated to dryness under reduced pressure, crude
  4. washwashed with DCM, aqueous layer
  5. extractionextracted with dichloromethane
  6. dry with materialOrganic layer dried over Na2SO4
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-80eb387bc97047c8a0acf1ff0f18676b
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07226921B2

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