Hydrochloric Acid → (2R)-2-{[10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl]-amino}-3-hydroxy-propionic acid

HRID 489585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489585
C[O:2][C:3](=[O:39])[C@H:4]([NH:7][C:8]([C:10]1[N:19]2[C:13]([CH2:14][N:15]([C:24](=[O:38])[C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=4)=[C:27]([CH3:37])[CH:26]=3)[C:16]3[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=3[CH2:18]2)=[CH:12][CH:11]=1)=[O:9])[CH2:5][OH:6].[OH-].[Na+].Cl>CC(C)=O>[C:31]1([C:28]2[CH:29]=[CH:30][C:25]([C:24]([N:15]3[C:16]4[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=4[CH2:18][N:19]4[C:10]([C:8]([NH:7][C@H:4]([CH2:5][OH:6])[C:3]([OH:39])=[O:2])=[O:9])=[CH:11][CH:12]=[C:13]4[CH2:14]3)=[O:38])=[CH:26][C:27]=2[CH3:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10208562HCID 10208562, Verbindung

Produkt 1

HCID 69793572(2R)-2-{[10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl]-amino}-3-hydroxy-propionic acidAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

(2R)-2-{[10-(4-Cyclohex-1-en-1-yl-3-methyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl]-amino}-3-hydroxy-propionic acid methyl ester of Example 13 (0.260 g, 0.493 mmol), was dissolved in acetone (3.3 mL), followed by the addition of 2.5 N sodium hydroxide (0.590 mL, 1.48 mmol). The reaction was stirred at room temperature overnight, acidified with 1 N hydrochloric acid and extracted with diethyl ether. The combined ether phases were extracted with 1 N sodium hydroxide and the basic extracts acidified with 2 N hydrochloric acid. The acidified extracts were extracted with diethyl ether and the combined ether extracts dried over anhydrous magnesium sulfate, filtered and concentrated to afford 0.250 g of the title compound as a white powder.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. extractionThe combined ether phases were extracted with 1 N sodium hydroxide
  3. extractionThe acidified extracts were extracted with diethyl ether
  4. dry with materialthe combined ether extracts dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-021e26e15ef748eba6fa52492b2d5abf
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977254B2

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