Hydrochloric Acid → 1,5-anhydro-3-(6-bromo-1-methyl-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2,3-dideoxy-L-threo-pentitol

HRID 1183147노트

반응식

HRID 1183147 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[NH:8][CH2:7][N:6]([C@H:16]1[CH2:21][CH2:20][O:19][CH2:18][C@@H:17]1[O:22][Si](C(C)(C)C)(C)C)[C:5]2=[O:30].Cl.[C:32]([O-])(O)=O.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=13)[N:8]([CH3:32])[CH2:7][N:6]([C@@H:16]1[C@@H:17]([OH:22])[CH2:18][O:19][CH2:20][CH2:21]1)[C:5]2=[O:30]

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 516892Sodium BicarbonateHCID 866903641,5-anhydro-3-(6-bromo-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2-O-[tert-butyl(dimethyl)silyl]-3,4-dideoxy-L-threo-pentitol

생성물 1

HCID 866903661,5-anhydro-3-(6-bromo-1-methyl-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2,3-dideoxy-L-threo-pentitol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1,5-anhydro-3-(6-bromo-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2-O-[tert-butyl(dimethyl)silyl]-3,4-dideoxy-L-threo-pentitol (0.89 g, 1.8 mmol) in THF (17.5 mL) was added hydrochloric acid (1 N, 10 mL). Additional concentrated hydrochloric acid (2 mL) was added. After stirring overnight, the solution was basified by addition of saturated, aqueous NaHCO3, then extracted 2× with EtOAc. The organics were washed with brine, dried over MgSO4, filtered, concentrated, and dried to provide 1,5-anhydro-3-(6-bromo-1-methyl-4-oxo-1,4-dihydrobenzo[h]quinazolin-3(2H)-yl)-2,3-dideoxy-L-threo-pentitol that gave a mass ion (ES+) of 392.9 for [M+H]+.

후처리

  1. extractionextracted 2× with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried

출처 및 근거

ORD 기록
ord-7f0ac6c2cdda457ebce2e4d49e79c9ed
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664234B2

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