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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
ノート
印刷プレビュー

反応式

HRID 1847009 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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 ester収率 47%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3f6bd7e7d80f4d6b8140f8aed81ac028
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08952010B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート