Tetrahydrofuran → HCID 86630235、化合物

HRID 641989ノート

反応式

HRID 641989 の反応式
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]

参加物

7

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 23667635Sodium periodateHCID 68511776methyl 3-[6-[(1E)-3-tert-butoxy-3-oxoprop-1-en-1-yl]-4-oxoquinazolin-3(4H)-yl]-4-methylbenzoate

生成物 1

HCID 86630235HCID 86630235、化合物

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-50e7c9b4821d472d8673124b7a4c1ac8
出典データセット
uspto-grants-2010_04
特許番号
US07696215B2

反応ノート

読み込み中…