Nitrogen → [2-(5-Oxo-hexyl)-oxazol-4-yl]-(5-phenyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

HRID 1189376ノート

反応式

HRID 1189376 の反応式
N#N.[C:3]([O:7][C:8](=[O:22])[NH:9][C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[O:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[H-].[Na+].[C:25]1([C:31]2[O:35][CH:34]=[N:33][C:32]=2[C:36](Cl)=[O:37])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.O>[C:3]([O:7][C:8](=[O:22])[N:9]([C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[O:13][CH:14]=1)[C:36]([C:32]1[N:33]=[CH:34][O:35][C:31]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:37])([CH3:6])([CH3:4])[CH3:5]

参加物

7

反応物 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 27763005-Phenyl-1,3-oxazole-4-carbonyl chlorideHCID 67128525[2-(5-Oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 67128650[2-(5-Oxo-hexyl)-oxazol-4-yl]-(5-phenyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester (65 mg, 0.23 mL) in THF (2.0 mL) was added to a suspension of NaH (12 mg, 0.28 mmol) in THF (1.0 mL) at 0° C. The resulting suspension was stirred at 0° C. for 5 min and at rt for 30 min. It was cooled to 0° C. and treated dropwise with a solution of the above prepared 5-phenyl-oxazole-4-carbonyl chloride in THF (1.0 mL). The resulting suspension was stirred for 30 min at 0° C. followed by 16 h at rt. Water was then added and the aq. layer was extracted several time with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1→2:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.39. LC-MS-conditions 02: tR=1.06 min, [M+H]+=454.20.

後処理

  1. temperatureIt was cooled to 0° C.
  2. additiontreated dropwise with a solution of the
  3. stirringThe resulting suspension was stirred for 30 min at 0° C.
  4. waitfollowed by 16 h at rt
  5. extractionthe aq. layer was extracted several time with EA
  6. dry with materialextracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the residue by FC (4:1→2:1 hept-EA)

出典と根拠

ORDレコード
ord-4b131ee75e474db79fcde7bfb1244d5f
出典データセット
uspto-grants-2014_03
特許番号
US08674111B2

反応ノート

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