Water → HCID 67549096、化合物

HRID 43899ノート

反応式

HRID 43899 の反応式
P(=O)(O)(O)O.C(OC([NH:13][CH:14]1[CH2:17][N:16]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:15]1)=O)(C)(C)C.C1COCC1.O>ClCCl>[NH2:13][CH:14]1[CH2:17][N:16]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:15]1

参加物

6

反応物 4

HCID 962WaterHCID 1004Phosphoric Acid2 回HCID 8028TetrahydrofuranHCID 67548952Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-6-carboxylate

生成物 1

HCID 67549096HCID 67549096、化合物収率 87.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

85% phosphoric acid (0.23 mL, 1.96 mmol) was added to a solution of ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-6-carboxylate obtained in Example (225b) (296 mg, 0.78 mmol) in dichloromethane (2 mL) at room temperature, followed by stirring for 27 hours. Then, THF (1 mL) and 85% phosphoric acid (0.23 mL, 1.96 mmol) were added, and the mixture was further stirred for five hours. Water was added to the reaction solution, and the mixture was washed with ethyl acetate. Then, a 1 N aqueous sodium hydroxide solution was added to the aqueous layer, followed by extraction with a chloroform/methanol mixed solvent. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the solvent was evaporated under reduced pressure to obtain 190 mg of the title compound as a milk white solid (87%).

後処理

  1. stirringthe mixture was further stirred for five hours
  2. washthe mixture was washed with ethyl acetate
  3. additionThen, a 1 N aqueous sodium hydroxide solution was added to the aqueous layer
  4. extractionfollowed by extraction with a chloroform/methanol mixed solvent
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThereafter, the solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-882dff2be03b4e539de5b9f40b7a7433
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

反応ノート

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