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Hydrochloric Acid → (7-(Benzyloxy)-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

HRID 495387
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HRID 495387 반응식
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH2:15][NH:16][C:17](=O)[NH:18]2)=[CH:13][C:12]=1[O:22][CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:24]([O:30][CH2:31]Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].Cl.CN(C=[O:38])C>C(OCC)(=O)C.O>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:38])[N:16]([CH2:31][O:30][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[CH:17]=[N:18]2)=[CH:13][C:12]=1[O:22][CH3:23])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 545382477-Benzyloxy-6-methoxy-3,4-dihydroquinazolinone

생성물 1

HCID 10834555(7-(Benzyloxy)-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (60% dispersion in mineral oil, 1.44 g) was added portionwise during 20 minutes to a solution of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolinone (8.46 g) in DMF (70 ml) and the mixture was stirred for 1.5 hours. Chloromethyl pivalate (5.65 g) was added dropwise and the mixture was stirred at ambient temperature for 2 hours. The mixture was diluted with ethyl acetate (100 ml) and poured onto a mixture of ice and water (400 ml) containing 2N aqueous hydrochloric acid (4 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. The residue was triturated under a mixture of petroleum ether (b.p. 60-80° C.) and diethyl ether. The solid so obtained was isolated and dried under vacuum to give 7-benzyloxy-6-methoxy-3-pivaloyloxymethyl-3,4dihydroquinazolin-4-one (10 g); NMR Spectrum: (DMSOd6) 1.11 (s, 9H), 3.89 (s, 3H), 5.3 (s, 2H), 5.9 (s, 2H), 7.27 (s, 1H), 7.35 (m, 1H), 7.47 (t, 2H), 7.49 (d, 2H), 7.51 (s, 1H), 8.34 (s, 1H).

후처리

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue was triturated under a mixture of petroleum ether (b.p. 60-80° C.) and diethyl ether
  9. customThe solid so obtained
  10. customwas isolated
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-e13d259b954e451e88712b48562bbc3e
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06939866B2

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