1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(4-(Azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazole

HRID 1172935노트

반응식

HRID 1172935 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].C1CCN2C(=NCCC2)CC1.P([N:52]=[N+:53]=[N-:54])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOCC>[N:52]([CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[O:14][N:13]=[C:12]([C:4]3[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:11])[CH3:10])=[C:2]([Cl:1])[CH:3]=3)[N:16]=2)=[CH:18][CH:19]=1)=[N+:53]=[N-:54]

참가 물질

7

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 516892Sodium BicarbonateHCID 59556551(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol

생성물 1

HCID 595565965-(4-(Azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazole수율 61.5%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenyl)methanol (0.100 g, 0.290 mmol) in THF (1.5 ml) was added DBU (0.048 ml, 0.319 mmol) followed by diphenyl phosphorazidate (0.069 ml, 0.319 mmol). After about 15 h the reaction mixture was poured into ether and saturated NaHCO3. The organic layer was separated, washed with brine, dried (MgSO4), concentrated in vacuo and purified by chromatography on silica gel (eluting with EtOAc/Hep) to provide 5-(4-(azidomethyl)phenyl)-3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazole (0.066 g, 60%) as a colorless solid. LCMS (Table 1, Method c) Rt=3.22 min, m/z 370 (M+H)+

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography on silica gel (eluting with EtOAc/Hep)

출처 및 근거

ORD 기록
ord-7360712153c949788c4f2a31abf877b8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834039B2

반응 노트

불러오는 중…