HCID 68752619, Verbindung → 2-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid

HRID 333296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333296
C([O:8][C:9](=[O:37])[CH2:10][C:11]1([C:16]([NH:18][CH2:19][CH:20]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CCO.[Pd]>[C:24]([O:23][C:21](=[O:22])[CH:20]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[CH2:19][NH:18][C:16]([C:11]1([CH2:10][C:9]([OH:37])=[O:8])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:17])([CH3:27])([CH3:25])[CH3:26]

Komponenten

4

Edukt 1

HCID 68752619HCID 68752619, Verbindung

Produkt 1

HCID 687477812-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acidAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoate (81.2 mg, 0.148 mmol) and Pd/C (31.5 mg, 0.015 mmol) in EtOH (1 ml) was allowed to stir under hydrogen atmosphere (1 atm) for 6.5 hr. The reaction mixture was filtered, and the filter cake was washed with MeOH. The combined filtrate was concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN) to give 2-(1-(3-tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid (30.6 mg); Retention time=1.30 minutes (condition B); MS (m+1)=458.2; 1H NMR (400 MHz, CDCl3, data for major rotamer) δ ppm 1.37 (s, 9H) 1.70-1.98 (m, 8H) 2.64-2.88 (m, 5H) 3.34-3.53 (m, 2H) 6.53-6.56 (m, 1H) 7.02-7.04 (m, 1H) 7.28 (d, J=2.0 Hz, 1H) 7.36 (d, J=8.0 Hz, 1H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with MeOH
  3. concentrationThe combined filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-7a378b70347343958732246d0b67a657
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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