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Hydrochloric Acid → 3-(Benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acid

HRID 1093120
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인쇄 미리보기

반응식

HRID 1093120 반응식
[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:12]2=[N:11][C:10]=1[C:23]([O:25]CC)=[O:24])[CH2:17][CH2:16]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O.Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[C:21](=[O:22])[N:13]2[CH2:14][CH:15]3[CH2:16][CH2:17][N:18]([C:12]2=[N:11][C:10]=1[C:23]([OH:25])=[O:24])[CH2:19][CH2:20]3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57904901Ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate

생성물 1

HCID 579050733-(Benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acid수율 89.1%

시약·촉매·용매 2

HCID 702
Ethanol
용매
HCID 962Water용매

실험 절차

A mixture of ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate (0.5491 g, 1.486 mmol) and LiOH.H2O (0.071 g, 2.97 mmol) in ethanol (12 mL) and water (3.00 mL) was stirred at room temperature for 6 h. The mixture was acidified with concentrated HCl and the product was extracted with ethyl acetate. The organic phase was washed with brine, then dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (0.4521 g, 89% yield). 1H NMR (500 MHz, CD3OD) δ: 7.53-7.49 (2H, m), 7.42-7.36 (3H, m), 5.27 (2H, d, J=15.3 Hz), 4.11-4.00 (4H, m), 3.96 (2H, d, J=14.0 Hz), 3.17-3.13 (1H, m), 2.45-2.39 (2H, m), 2.10-2.03 (2H, m). LCMS (M+H) calcd for C18H20N3O4: 342.14; found: 342.20.

후처리

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-dc765f070c604140a3333a000389e5e6
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129398B2

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