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Benzyl Alcohol → [5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid benzyl ester

HRID 1847009
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HRID 1847009 반응식
[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]3[O:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=3[N:16]=2)[CH2:5][CH:4](C(O)=O)[CH2:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C.[CH2:45]([OH:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C1C=CC=CC=1>[CH2:45]([O:52][C:43](=[O:28])[NH:40][CH:4]1[CH2:3][C:2](=[O:1])[N:6]([C:7]2[CH:8]=[CH:9][C:10]3[O:11][CH2:12][C:13](=[O:17])[NH:14][C:15]=3[N:16]=2)[CH2:5]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1
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참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 867249395-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid

생성물 1

HCID 86724940[5-Oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-yl]carbamic acid benzyl ester수율 47%

시약·촉매·용매

1
HCID 241Benzene용매

실험 절차

A mixture of 5-oxo-1-(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)pyrrolidin-3-carboxylic acid (764 mg, 2.76 mmol), diphenyl phosphoryl azide (0.891 ml, 4.13 mmol), triethylamine (0.626 ml, 4.49 mmol) and benzene (35 ml) was heated under reflux for 3 hours. Benzyl alcohol (21 ml) was added to the reaction solution, which was further heated under reflux overnight. After cooling, the insoluble material was removed by filtration, the filtrate was diluted with ethyl acetate, washed with a saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate and chloroform/methanol) to yield 496 mg (47%) of the title compound in the form of a light yellow solid.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperaturewas further heated
  4. temperatureunder reflux overnight
  5. temperatureAfter cooling
  6. customthe insoluble material was removed by filtration
  7. additionthe filtrate was diluted with ethyl acetate
  8. washwashed with a saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate and chloroform/methanol)

출처 및 근거

ORD 기록
ord-3f6bd7e7d80f4d6b8140f8aed81ac028
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952010B2

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