Propylphosphonic anhydride → Methyl {4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate
反応式
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[O:19]=[C:20]1[NH:25][C:24]2[CH:26]=[C:27]([C:30]([OH:32])=O)[CH:28]=[CH:29][C:23]=2[O:22][CH2:21]1.[O:33]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[NH:36][CH:35]([CH2:43][C:44]([O:46][CH3:47])=[O:45])[CH2:34]1>CCOC(C)=O>[O:19]=[C:20]1[NH:25][C:24]2[CH:26]=[C:27]([C:30]([N:36]3[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[O:33][CH2:34][CH:35]3[CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:32])[CH:28]=[CH:29][C:23]=2[O:22][CH2:21]1参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 75 °C
実験手順
T3P (50% solution in EtOAc, 61.5 g, 96.6 mmol) was added to 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid (10.3 g, 53.1 mmol), methyl 3,4-dihydro-2H-1,4-benzoxazin-3-ylacetate (Intermediate 2, 10.0 g, 48.3 mmol) and TEA (26.8 mL, 193.2 mmol) in EtOAc (125 mL) at rt. The resulting mixture was stirred at 75° C. for 16 h. The resulting solution was diluted with 350 mL of EtOAc and washed with sat. aq. NaHCO3 solution (160 mL), 0.5 M HCl solution (160 mL) and brine (160 mL). The organic phase was dried over anhydrous Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by re-crystallization from MeOH to afford the title compound (10.1 g, 55%) as a white solid.
後処理
- washwashed with sat. aq. NaHCO3 solution (160 mL), 0.5 M HCl solution (160 mL) and brine (160 mL)
- dry with materialThe organic phase was dried over anhydrous Na2SO4
- filtrationfiltered
- customevaporated
- customto afford crude product
- customThe crude product was purified by re-crystallization from MeOH
出典と根拠
- ORDレコード
- ord-9654556a980e49c5994b4bc23e9714a5
- 出典データセット
- uspto-grants-2016_07
- 特許番号
- US09394291B2
反応ノート
読み込み中…