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

HRID 43924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43924
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

Komponenten

5

Edukt 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

Produkt 1

HCID 67549645Ethyl 2-[(1R,5R)-2,6-diazabicyclo[3.2.0]hept-6-yl]-4-methyl-1,3-thiazole-5-carboxylateAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-eeadcb480f424924b11cd4f71d7b3c73
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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