Hydrochloric Acid → (R)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 352377

Reaktionsgleichung

Reaktionsgleichung von HRID 352377
[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][C@@H:10]([NH:25]C(OC(C)(C)C)=O)[C:9]1=[O:33])=[O:6])([CH3:4])([CH3:3])[CH3:2].Cl.O.C(OCC)C>C(O)C>[C:1]([C:5]([CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][C@@H:10]([NH2:25])[C:9]1=[O:33])=[O:6])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 12043265(R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Produkt 1

HCID 11190074(R)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 63.5 g of (R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine in 100 ml of ethanol was added 100 ml of 6N hydrochloric acid. The mixture was stirred at 60° C. for 1.5 hours. After the reaction mixture was cooled to room temperature, a mixed solvent of water and diethyl ether (1:1) was added. The aqueous layer was separated, neutralized with a 6N aqueous solution of sodium hydroxide, and then extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure, whereby 46.3 g of (R)-(−)-1-tert-butylcarbonylmethyl-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine was obtained.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d3610f679fbf416bbd60b2c9044db414
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747022B2

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