(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acid → HCID 87798160, Verbindung

HRID 133072

Reaktionsgleichung

Reaktionsgleichung von HRID 133072
Cl.[CH:2]1([CH2:5][CH:6]2[NH:11][CH2:10][CH2:9][N:8]3[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=[C:7]23)[CH2:4][CH2:3]1.[C:19]([O:23][C:24]([NH:26][C@H:27]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41])[CH2:28][C:29](O)=[O:30])=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([NH:26][C@H:27]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41])[CH2:28][C:29]([N:11]1[CH2:10][CH2:9][N:8]2[N:12]=[C:13]([C:15]([F:16])([F:18])[F:17])[N:14]=[C:7]2[CH:6]1[CH2:5][CH:2]1[CH2:4][CH2:3]1)=[O:30])=[O:25])([CH3:22])([CH3:20])[CH3:21]

Komponenten

3

Edukt 2

HCID 7146288(R)-3-(tert-butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic acidHCID 69361152HCID 69361152, Verbindung

Produkt 1

HCID 87798160HCID 87798160, Verbindung

Versuchsvorschrift

A 35 mg portion of 8-(cyclopropylmethyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine hydrochloride was coupled to (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,4,5-trifluorophenyl)butanoic acid essentially following the procedure outlined in Example 2, Step D, with the following exception. The reaction mixture was stirred at ambient temperature for 24 h and then concentrated. The residue was purified by preparative TLC (silica gel, 10% methanol/dichloromethane) to provide 54 mg of the title compound as a mixture of diastereomers. The diastereomers were separated by HPLC (OD chiralcel column, 7% ethanol/hexane) to give the faster eluting diastereomer and the slower eluting diastereomer.

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was purified by preparative TLC (silica gel, 10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-60fbc05d4a2e45658c86f603e0a247ba
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390809B2

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