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 577909ノート

反応式

HRID 577909 の反応式
[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

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 673572055-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carbohydrazide2 回

生成物 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)-one収率 97%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-0338ae7ea56341f39bf45c847cb9f82a
出典データセット
uspto-grants-2015_05
特許番号
US09040528B2

反応ノート

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