Hydrochloric Acid → (2R)-2-amino-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

HRID 2070144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070144
[CH3:1][CH:2]([CH3:39])[CH2:3][C@@H:4]([NH:31]C(=O)OC(C)(C)C)[C:5](=[O:30])[NH:6][CH:7]1[CH2:16][C:15]2[C:10](=[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[C:8]1=[O:29].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:31][C@H:4]([CH2:3][CH:2]([CH3:39])[CH3:1])[C:5]([NH:6][CH:7]1[CH2:16][C:15]2[C:10](=[C:11]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[C:8]1=[O:29])=[O:30]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59620371HCID 59620371, Verbindung

Produkt 1

HCID 44193593(2R)-2-amino-4-methyl-N-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-yl]pentanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

tert-Butyl (2R)-4-methyl-1-oxo-1-[2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino]pentan-2-ylcarbamate (588 mg) was dissolved in ethanol (2.9 mL), and concentrated hydrochloric acid (1.2 mL) was added thereto. The mixture was heated at 50° C. while being stirred for 30 minutes. The resultant mixture was neutralized with saturated sodium bicarbonate solution under cooling on ice. Subsequently, the mixture was extracted with ethyl acetate, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was washed with saturated sodium chloride solution, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (416 mg) was yielded.

Aufarbeitung

  1. temperatureunder cooling on ice
  2. extractionSubsequently, the mixture was extracted with ethyl acetate
  3. extractionthe aqueous layer was further extracted with ethyl acetate
  4. washthe combined organic layer was washed with saturated sodium chloride solution
  5. dry with materialby drying over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, whereby the title compound (416 mg)
  7. customwas yielded

Quellen und Nachweise

ORD-Eintrag
ord-77f65a9a379b4418bec0b70a09f6325f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299255B2

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