Potassium Carbonate → (S)-2-[4-(3-tert-butoxycarbonylaminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

HRID 63741

Reaktionsgleichung

Reaktionsgleichung von HRID 63741
[CH2:1]([O:4][C:5](=[O:37])[C@@H:6]([NH:25][C:26](=[O:36])[C:27]1[C:32]([Cl:33])=[CH:31][C:30]([OH:34])=[CH:29][C:28]=1[Cl:35])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:10][CH:9]=1)[CH2:2][CH3:3].[C:38]([O:42][C:43]([NH:45][CH2:46][CH2:47][CH2:48]Br)=[O:44])([CH3:41])([CH3:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:4][C:5](=[O:37])[C@@H:6]([NH:25][C:26](=[O:36])[C:27]1[C:28]([Cl:35])=[CH:29][C:30]([O:34][CH2:48][CH2:47][CH2:46][NH:45][C:43]([O:42][C:38]([CH3:39])([CH3:41])[CH3:40])=[O:44])=[CH:31][C:32]=1[Cl:33])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[C:15](=[O:24])[N:16]([CH3:23])[C:17](=[O:22])[N:18]([CH3:21])[C:19]=2[CH3:20])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 89720687(S)-2-(2,6-dichloro-4-hydroxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Produkt 1

HCID 89721106(S)-2-[4-(3-tert-butoxycarbonylaminopropoxy)-2,6-dichlorobenzoylamino]-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester

Versuchsvorschrift

The title compound was prepared using a similar procedure as described in Example 5, Step 5, starting from (S)-2-(2,6-dichloro-4-hydroxy-benzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid propyl ester (558 mg, 1.07 mmol), 3-tert-butoxycarbonylaminopropyl bromide (306 mg, 1.28 mmol), and potassium carbonate (445 mg, 3.22 mmol), and after ISCO column chromatography purification, resulted in a white solid (654 mg, 87%). ES(+)-HRMS m/e calcd. for C34H42Cl2N4O8 (M+H)+ 705.2453, obsd. 705.2451.

Aufarbeitung

  1. customafter ISCO column chromatography purification

Quellen und Nachweise

ORD-Eintrag
ord-e068bf94fe6044e39065a3cb9ea12828
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447035B2

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