Propylphosphonic anhydride → Ethyl {4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate

HRID 1054161ノート

反応式

HRID 1054161 の反応式
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.[CH2:33]([O:35][C:36](=[O:48])[CH2:37][CH:38]1[NH:43][C:42]2[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=2[O:40][CH2:39]1)[CH3:34]>CCOC(C)=O>[O:19]=[C:20]1[NH:25][C:24]2[CH:26]=[C:27]([C:30]([N:43]3[C:42]4[CH:44]=[CH:45][CH:46]=[CH:47][C:41]=4[O:40][CH2:39][CH:38]3[CH2:37][C:36]([O:35][CH2:33][CH3:34])=[O:48])=[O:32])[CH:28]=[CH:29][C:23]=2[O:22][CH2:21]1

参加物

5

反応物 3

HCID 111923Propylphosphonic anhydrideHCID 7061213-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acidHCID 10632771Ethyl 3,4-dihydro-2H-1,4-benzoxazine-3-acetate

生成物 1

HCID 131736322Ethyl {4-[(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)carbonyl]-3,4-dihydro-2H-1,4-benzoxazin-3-yl}acetate収率 35.2%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
75 °C

実験手順

T3P (50% solution in EtOAc, 132.4 g, 0.208 mol) was added to 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylic acid (22.1 g, 0.114 mol), ethyl-2-(3,4-dihydro-2H-1,4-benzoxazin-3-yl)acetate (23.0 g, 0.104 mol) and TEA (57.9 mL, 0.416 mol) in EtOAc (139 mL) at rt. The resulting mixture was stirred at 75° C. for 16 h. The resulting solution was diluted with 800 mL of EtOAc and washed with aq. sat. NaHCO3 solution (300 mL), 0.5 M HCl solution (300 mL) and brine (300 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 (14.5 g, 35%) as a white solid.

後処理

  1. washwashed with aq. sat. NaHCO3 solution (300 mL), 0.5 M HCl solution (300 mL) and brine (300 mL)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified by re-crystallization from MeOH

出典と根拠

ORDレコード
ord-19a9a3e9c6e74b3e92e09e7e477da0b1
出典データセット
uspto-grants-2016_07
特許番号
US09394291B2

反応ノート

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