Ethanol → LBQ-657

HRID 882540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882540
C([O:3][C:4](=[O:29])[C@H:5]([CH3:28])[CH2:6][C@H:7]([N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C.[OH-].[Na+].C1C[O:35]CC1.C(O)C>O>[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:14][C:9]([CH2:8][C@@H:7]([NH:21][C:25](=[O:26])[CH2:24][CH2:23][C:22]([OH:27])=[O:35])[CH2:6][C@@H:5]([CH3:28])[C:4]([OH:3])=[O:29])=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66739220Ethyl (2R,4S)-4-([1,1'-biphenyl]-4-ylmethyl)-2-methyl-4-(2,5-dioxopyrrolidin-1-yl)butanoate

Produkt 1

HCID 10430040LBQ-657

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

(2R,4S)-5-Biphenyl-4-yl-4-(2,5-dioxopyrrolidin-1-yl)-2-methylpentanoic acid ethyl ester (590 mg) is added to a mixture of 1 M NaOH (2.75 ml), THF (9 ml) and ethanol (9 ml). The mixture is stirred for 16 h. The mixture is diluted with water (20 ml) and extracted with isopropyl acetate. The water phase is acidified with 1 M HCl (5 ml) and extracted with isopropyl acetate. The combined organic phases are dried (MgSO4) and concentrated in vacuo to give (2R,4S)-5-Biphenyl-4-yl-4-(3-carboxypropionylamino)-2-methyl-pentanoic acid (3-a, R1=4-oxo-pentanoic acid, R2=H, R3=H). 1H NMR (DMSO): 1.05 (2H), 1.35 (1H), 1.79 (1H), 2.29 (2H), 2.39 (3H), 2.70 (2H), 3.97 (1H), 7.25 (2H), 7.34 (1H), 7.44 (2H), 7.56 (2H), 7.63 (2H), 7.74 (1H), 12.01 (2H).

Aufarbeitung

  1. extractionextracted with isopropyl acetate
  2. extractionextracted with isopropyl acetate
  3. dry with materialThe combined organic phases are dried (MgSO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-34fdc94d5fe443f1a094cd55a4d9dd68
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993785B2

Notizen zur Reaktion

Wird geladen…