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

HRID 1887752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887752
[CH3:1][C:2]([NH:38]C(=O)OC(C)(C)C)([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:7](=[O:32])[NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[C:10]1=[O:31])=[O:4].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:38][C:2]([CH3:1])([CH3:37])[C:3]([NH:5][C@H:6]([CH2:33][CH:34]([CH3:35])[CH3:36])[C:7]([NH:8][CH:9]1[CH2:18][C:17]2[C:12](=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:25][C:26]2[CH:30]=[CH:29][S:28][CH:27]=2)[C:10]1=[O:31])=[O:32])=[O:4]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 44193590tert-butyl 2-methyl-1-[(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-ylamino]-1-oxopropan-2-ylcarbamate

Produkt 1

HCID 59620332(2R)-2-(2-amino-2-methylpropanamido)-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
70 °C

Versuchsvorschrift

tert-Butyl 2-methyl-1-[(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-ylamino]-1-oxopropan-2-ylcarbamate (2.8 g) was dissolved in ethanol (28 mL), and concentrated hydrochloric acid (7.5 mL) was added thereto. The mixture was heated at 70° C. while being stirred for 30 minutes, and then neutralized with saturated aqueous sodium bicarbonate solution under cooling on ice. Subsequently, the resultant mixture was extracted with chloroform and water, and the aqueous layer was further extracted with chloroform. The organic layers were combined. The combined organic layer was washed with saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (2.30 g) was yielded.

Aufarbeitung

  1. temperatureunder cooling on ice
  2. extractionSubsequently, the resultant mixture was extracted with chloroform and water
  3. extractionthe aqueous layer was further extracted with chloroform
  4. washThe combined organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure, whereby the title compound (2.30 g)
  7. customwas yielded

Quellen und Nachweise

ORD-Eintrag
ord-84013b6b36a148e3abe362994e14b75a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501772B2

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