Formic Acid → (R)-3-[[N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl)glycyl]amino]pyrrolidine

HRID 1280953

Reaktionsgleichung

[C:1]([O:5][C:6]([NH:8][C:9]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][C@@H:18]1[CH2:22][CH2:21][N:20](CC2C=CC(Cl)=CC=2)[CH2:19]1)=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)=O>[OH-].[OH-].[Pd+2].CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][C:10]=1[C:11]([NH:13][CH2:14][C:15]([NH:17][C@@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1)=[O:16])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of (R)-3-[{N-(2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl}glycyl)amino]-1-(4-chlorobenzyl)pyrrolidine (6.3 g, 11.4 mmol), Pd(OH)2 (1.68 g), HCO2H (3.7 mL), and methanol (80 mL) was stirred at 50° C. overnight. After the mixture was cooled to room temperature, the Pd catalyst was filtered off through Celite and the filtrate was concentrated. Column chromatography (SiO2, AcOEt, AcOEt/MeOH=5/1-4/1) gave (R)-3-[{N-2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl}glycyl]aminolpyrrolidine (4.42 g, 90%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ1.48 (s, 9 H), 2.0-2.4 (m, 2 H), 3.42-3.71 (m, 5 H), 4.00-4.22 (m, 2 H), 4.56 (br, 1 H), 7.48 (d, J=9.0 Hz, 1 H), 7.93 (s, 1 H), 8.17 (br, 1 H), 8.33 (d, J=9.0 Hz, 1 H), 8.45 (br, 1 H).

Aufarbeitung

temperatureAfter the mixture was cooled to room temperature
filtrationthe Pd catalyst was filtered off through Celite
concentrationthe filtrate was concentrated
customColumn chromatography (SiO2, AcOEt, AcOEt/MeOH=5/1-4/1) gave (R)-3-[{N-2-(tert-butoxycarbonylamino)-5-trifluoromethylbenzoyl}glycyl]aminolpyrrolidine (4.42 g, 90%) as a white solid

Quellen und Nachweise

ORD-Eintrag: ord-40f7895751fe400995029ec5b8ce2489
Quelldatensatz: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06451842B1

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