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 1054161노트

반응식

HRID 1054161 반응식
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

참가 물질

5

반응물 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

생성물 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}acetate수율 35.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

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온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19a9a3e9c6e74b3e92e09e7e477da0b1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394291B2

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