Sec-Butylamine → 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-sec-butylamino-3-chloro-5-fluorobenzoic acid ethyl ester

HRID 10293

Reaktionsgleichung

Reaktionsgleichung von HRID 10293
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[C:7]([Cl:25])[C:6]=1F)[CH3:2].[CH:28]([NH2:32])([CH2:30][CH3:31])[CH3:29]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[C:7]([Cl:25])[C:6]=1[NH:32][CH:28]([CH2:30][CH3:31])[CH3:29])[CH3:2]

Komponenten

4

Edukt 2

HCID 24874Sec-ButylamineHCID 586818944-[(S)-3-tert-Butoxycarbonylaminopyrrolidin-1-yl]-3-chloro-2,5-difluorobenzoic acid ethyl ester

Produkt 1

HCID 866071304-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-sec-butylamino-3-chloro-5-fluorobenzoic acid ethyl esterAusbeute 167,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

4-[(S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2,5-difluorobenzoic acid ethyl ester (Example 2c, 1.95 g, 4.81 mmol), sec-butylamine (30 mL, 296 mmol), and dimethyl sulfoxide (20 mL) are heated in a sealed glass tube at 110° C. for 24 hours. The reaction mixture is evaporated, and purification by column chromatography (1:8, ethyl acetate/hexanes) provides the title compound as a yellow syrup (3.69 g). MS EI: m/z 458 (MH+).

Aufarbeitung

  1. customThe reaction mixture is evaporated
  2. custompurification by column chromatography (1:8, ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c9ad7ba81a844b13b2fa7d7f9fd4ed34
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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