L-Lysine → (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid L-lysine salt

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Reaktionsgleichung

[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12.[NH2:34][C@H:35]([C:41]([OH:43])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40]>C(#N)C>[NH2:34][C@H:35]([C:41]([OH:43])=[O:42])[CH2:36][CH2:37][CH2:38][CH2:39][NH2:40].[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[N:4]2[CH2:27][CH2:28][C@H:29]([CH2:30][C:31]([OH:33])=[O:32])[C:3]=12

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

(R)-2-(9-Chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid (2.0 g, 4.15 mmol) was dissolved in acetonitrile (66 mL) with heating (70° C., oil bath) and a 2.0 M aqueous L-lysine solution (2.075 mL, 4.15 mmol) was added. After addition, the oil bath was turned off, and the reaction was allowed to slowly cool to room temperature and stirred for 16 h. The white solid was collected by vacuum filtration to afford 2.365 grams of the desired (R)-2-(9-chloro-7-(4-isopropoxy-3-(trifluoromethyl)benzyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic acid L-lysine salt (91% yield).

Aufarbeitung

additionAfter addition
temperatureto slowly cool to room temperature
filtrationThe white solid was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag: ord-1a20ffe1eb8440d485b580d9c314a2ab
Quelldatensatz: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09085581B2

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