(R)-benzyl 3-(4-butoxy-4-oxobutanamido)-4-(3'-chlorobiphenyl-4-yl)butanoate → HCID 59607872, Verbindung

HRID 1945008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945008
[CH2:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][C:9]([NH:11][C@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)=[CH:27][CH:26]=1)[CH2:13][C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:10])[CH2:2][CH2:3][CH3:4]>CCOC(C)=O.[Pd]>[CH2:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][C:9]([NH:11][C@H:12]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=2)=[CH:27][CH:26]=1)[CH2:13][C:14]([OH:16])=[O:15])=[O:10])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 1

HCID 59607868(R)-benzyl 3-(4-butoxy-4-oxobutanamido)-4-(3'-chlorobiphenyl-4-yl)butanoate

Produkt 1

HCID 59607872HCID 59607872, VerbindungAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of (R)-benzyl 3-(4-butoxy-4-oxobutanamido)-4-(3′-chlorobiphenyl-4-yl)butanoate (178.9 mg, 0.334 mmol) and Pd/C (71.0 mg, 0.033 mmol) in EtOAc (3 ml) is allowed to stir under hydrogen at room temperature for 1.5 hours. The reaction mixture is filtered, and concentrated to give crude. The resulting residue is purified by preparative HPLC using a gradient of 20% MeCN/water (0.1% TFA) to 100% MeCN to give (R)-3-(4-butoxy-4-oxobutanamido)-4-(3′-chlorobiphenyl-4-yl)butanoic acid (90.7 mg) as a white solid; HPLC retention time=1.27 minutes (condition B); MS (m+1)=446.24; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.91 (t, J=7.5 Hz, 3H) 1.31-1.40 (m, 2H) 1.55-1.62 (m, 2H) 2.43-2.47 (m, 2H) 2.52-2.69 (m, 4H) 2.93 (A of ABX, Jab=3.7 Hz, Jax=7.7 Hz, 1H) 3.00 (B of ABX, Jab=13.7 Hz, Jbx=6.8 Hz, 1H) 4.07 (t, J=6.7 Hz, 2H) 4.49-4.57 (m, 1H) 6.31 (br d, J=8.6 Hz, 1H) 7.26-7.37 (m, 4H) 7.43-7.46 (m, 1H) 7.49-7.52 (m, 2H) 7.55 (br t, J=1.8 Hz, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered
  2. concentrationconcentrated
  3. customto give crude
  4. customThe resulting residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e8d7465e0f954e3f83ab808f45ecb585
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394853B2

Notizen zur Reaktion

Wird geladen…