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 1887767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887767
Cl.[CH3:2][C:3]([NH:39]C(=O)OC(C)(C)C)([CH3:38])[C:4]([NH:6][C@H:7]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:8](=[O:33])[NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:5].[OH-].[Na+]>O1CCCC1>[NH2:39][C:3]([CH3:2])([CH3:38])[C:4]([NH:6][C@H:7]([CH2:34][CH:35]([CH3:36])[CH3:37])[C:8]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[C:14]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:11]1=[O:32])=[O:33])=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
48 °C

Versuchsvorschrift

Concentrated hydrochloric acid (89.6 mL) was added to the tetrahydrofuran solution of 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, and the mixture was stirred at an internal temperature of 48±2° C. for 30 minutes. The mixture was neutralized with 25% aqueous sodium hydroxide solution (172 g) under cooling on an ice bath. The organic layer was separated, and then concentrated under reduced pressure, whereby the title compound (49.36 g) was yielded.

Aufarbeitung

  1. temperatureunder cooling on an ice bath
  2. customThe organic layer was separated
  3. concentrationconcentrated under reduced pressure, whereby the title compound (49.36 g)
  4. customwas yielded

Quellen und Nachweise

ORD-Eintrag
ord-5b45015e40dc4b2ca0eb118f99ef59dd
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501772B2

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