1,1'-Carbonyldiimidazole → 5-(5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazol-3-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 577909노트

반응식

HRID 577909 반응식
[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:34]2[CH2:39][C@H:38]([CH3:40])[O:37][C@H:36]([CH3:41])[CH2:35]2)=[C:22]([F:33])[C:23]2[O:27][N:26]=[C:25]([C:28]([NH:30][NH2:31])=[O:29])[C:24]=2[CH:32]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1([C:47](N2C=CN=C2)=[O:48])C=CN=C1.CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[Si:1]([O:18][CH2:19][C:20]1[C:21]([N:34]2[CH2:35][C@H:36]([CH3:41])[O:37][C@H:38]([CH3:40])[CH2:39]2)=[C:22]([F:33])[C:23]2[O:27][N:26]=[C:25]([C:28]3[O:29][C:47](=[O:48])[NH:31][N:30]=3)[C:24]=2[CH:32]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 673572055-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carbohydrazide2회

생성물 1

HCID 673579695-(5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazol-3-yl)-1,3,4-oxadiazol-2(3H)-one수율 97%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

5-((tert-Butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carbohydrazide (Intermediate 207, 490 mg, 0.85 mmol) and di(1H-imidazol-1-yl)methanone (207 mg, 1.27 mmol) were dissolved in 8 ml of THF and was treated with DIEA (297 μl, 1.70 mmol) at room temperature for 16 hours. Reaction diluted with ethyl acetate and quenched with aq. Ammonium chloride solution. Organic layer was separated and washed with water, dried over sodium sulfate and concentrated to give 5-(5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazol-3-yl)-1,3,4-oxadiazol-2(3H)-one (495 mg, 97%)

후처리

  1. customReaction
  2. customquenched with aq. Ammonium chloride solution
  3. customOrganic layer was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0338ae7ea56341f39bf45c847cb9f82a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040528B2

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