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

HRID 1189382노트

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HRID 1189382 반응식
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+].[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:36][CH:35]=[N:34][C:33]=2[C:37](Cl)=[O:38])=[CH:28][CH:27]=1>C1COCC1.O>[C:3]([O:7][C:8](=[O:22])[N:9]([C:37]([C:33]1[N:34]=[CH:35][O:36][C:32]=1[C:29]1[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=1)=[O:38])[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])([CH3:4])[CH3:5]

참가 물질

7

반응물 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 67128525[2-(5-Oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl esterHCID 86664909HCID 86664909, 화합물

생성물 1

HCID 67128482[5-(4-Fluoro-phenyl)-oxazole-4-carbonyl]-[2-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

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온도
0 °C

실험 절차

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 (50 mg, 0.18 mL) in THF (1.0 mL) was added to a suspension of NaH (19 mg, 0.43 mmol) in THF (0.5 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-(4-fluoro-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 (6:4 hept-EA) gave the title compound as a yellow oil. TLC: rf (6:4 hept-EA)=0.21. LC-MS-conditions 02: tR=1.07 min, [M+H]+=472.48.

후처리

  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 (6:4 hept-EA)

출처 및 근거

ORD 기록
ord-b576851d78c443239a05e591fa814990
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674111B2

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