Water → Ethyl 2-[(1R,5R)-2,6-diazabicyclo[3.2.0]hept-6-yl]-4-methyl-1,3-thiazole-5-carboxylate

HRID 43924ノート

反応式

HRID 43924 の反応式
P(=O)(O)(O)O.[CH2:6]([O:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH2:22][C@@H:21]3[C@H:17]2[CH2:18][CH2:19][N:20]3C(OC(C)(C)C)=O)=[N:13][C:12]=1[CH3:30])=[O:10])[CH3:7].O>ClCCl>[C@@H:21]12[CH2:22][N:16]([C:14]3[S:15][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])=[C:12]([CH3:30])[N:13]=3)[C@@H:17]1[CH2:18][CH2:19][NH:20]2

参加物

5

反応物 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 86648822tert-Butyl (1R,5R)-6-[5-(ethoxycarbonyl)-4-methyl-1,3-thiazol-2-yl]-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

生成物 1

HCID 67549645Ethyl 2-[(1R,5R)-2,6-diazabicyclo[3.2.0]hept-6-yl]-4-methyl-1,3-thiazole-5-carboxylate収率 86.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

85% phosphoric acid (0.44 mL, 3.78 mmol) was added to a solution of tert-butyl (1R,5R)-6-[5-(ethoxycarbonyl)-4-methyl-1,3-thiazol-2-yl]-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate obtained in Example (236b) (278 mg, 0.76 mmol) in dichloromethane (1 mL) at room temperature, followed by stirring for two 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 an ethyl acetate/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 175 mg of the title compound as a pale yellow oily substance (87%).

後処理

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

出典と根拠

ORDレコード
ord-eeadcb480f424924b11cd4f71d7b3c73
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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