Tetrahydrofuran → HCID 86630235, 화합물

HRID 641989노트

반응식

HRID 641989 반응식
C(OC(=O)/C=C/[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]([C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23])[C:12]2=[O:30])(C)(C)C.I([O-])(=O)(=O)=O.[Na+].C1C[O:41][CH2:40]C1>O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[CH:40]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]([C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23])[C:12]2=[O:30])=[O:41]

참가 물질

7

반응물 3

HCID 8028Tetrahydrofuran2회HCID 23667635Sodium periodateHCID 68511776methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

생성물 1

HCID 86630235HCID 86630235, 화합물

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

To a mixture of methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate (1.11 g) and sodium periodate (1.24 g) in THF (20 ml) and water (6 ml) was added 2.5% wt solution of osmium tetroxide in tert-butanol (0.34 ml). The reaction was stirred at room temperature for 72 hours, diluted with THF (30 ml) and the precipitate removed by filtration. The resultant solution was concentrated and the residue dissolved in ethyl acetate, washed water/brine mixture, 10% aqueous solution of sodium thiosulfate (×2) and brine. The organic layers were concentrated to give a solid which was triturated with iso-hexane and collected by filtration to give methyl 3-(6-formyl-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate as a solid (0.54 g). NMR Spectrum: (DMSOd6) 2.21 (s, 3H), 3.88 (s, 3H), 7.64 (d, 1H), 7.93 (d, 1H), 8.05 (m, 1H), 8.11 (d, 1H), 8.32 (m, 1H), 8.48 (s, 1H), 8.77 (d, 1H), 10.19 (s, 1H); Mass Spectrum: M+H+ 323.

후처리

  1. customthe precipitate removed by filtration
  2. concentrationThe resultant solution was concentrated
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washwashed water/brine mixture, 10% aqueous solution of sodium thiosulfate (×2) and brine
  5. concentrationThe organic layers were concentrated
  6. customto give a solid which
  7. customwas triturated with iso-hexane
  8. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-50e7c9b4821d472d8673124b7a4c1ac8
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696215B2

반응 노트

불러오는 중…