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Nitrogen → [2-(5,5-Difluoro-hexyl)-oxazol-4-yl]-(2-methyl-5-m-tolyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

HRID 1189371
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HRID 1189371 반응식
N#N.[C:3]([O:7][C:8](=[O:23])[NH:9][C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[CH3:20])[O:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[H-].[Na+].[CH3:26][C:27]1[O:28][C:29]([C:35]2[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=2)=[C:30]([C:32](Cl)=[O:33])[N:31]=1>C1COCC1.O>[C:3]([O:7][C:8](=[O:23])[N:9]([C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[CH3:20])[O:13][CH:14]=1)[C:32]([C:30]1[N:31]=[C:27]([CH3:26])[O:28][C:29]=1[C:35]1[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=1)=[O:33])([CH3:6])([CH3:4])[CH3:5]
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7

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HCID 947NitrogenHCID 24758Sodium hydrideHCID 67128519[2-(5,5-Difluoro-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl esterHCID 866649052-Methyl-5-m-tolyl-oxazole-4-carbonyl chloride

생성물 1

HCID 67128661[2-(5,5-Difluoro-hexyl)-oxazol-4-yl]-(2-methyl-5-m-tolyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 962
Water
용매
HCID 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-(5,5-difluoro-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester (74 mg, 0.24 mL) in THF (2.0 mL) was added to a suspension of NaH (26 mg, 0.60 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 2-methyl-5-m-tolyl-oxazole-4-carbonyl chloride in THF (1.5 mL). The resulting suspension was stirred for 30 min at 0° C. followed by 2 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 (7:3 hept-EA) gave the title compound as a colorless oil. TLC: rf (7:3 hept-EA)=0.18. LC-MS-conditions 02: tR=1.17 min, [M+H]+=504.17.

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 2 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 (7:3 hept-EA)

출처 및 근거

ORD 기록
ord-e3a5c30c917b490db317b75fe5a7b1e2
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08674111B2

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