Lithium hydroxide, monohydrate → [(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethylamino}-Pyridine-3-Carbonyl)-Amino]-Acetic Acid

HRID 11690Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 11690
C[O:2][C:3](=[O:35])[CH2:4][NH:5][C:6]([C:8]1[C:9]([NH:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:7].O.[OH-].[Li+]>O1CCCC1.CO.O>[Cl:14][C:12]1[CH:13]=[C:8]([C:6]([NH:5][CH2:4][C:3]([OH:35])=[O:2])=[O:7])[C:9]([NH:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[N:10][CH:11]=1

Komponenten

6

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 69655399[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-pyridine-3-carbonyl)-amino]-acetic Acid Methyl Ester

Produkt 1

HCID 69655354[(5-Chloro-2-{2-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]-2-Oxo-Ethylamino}-Pyridine-3-Carbonyl)-Amino]-Acetic AcidAusbeute 52,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of [(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethylamino}-pyridine-3-carbonyl)-amino]-acetic acid methyl ester (0.043 g, 0.085 mmol) in tetrahydrofuran (1 mL), methanol (1 mL) and water (0.25 mL) was added lithium hydroxide monohydrate (0.018 g, 0.43 mmol). The reaction was stirred overnight. The reaction was then concentrated in vacuo, diluted with dichloromethane and passed through a fritted funnel. The filtrate was treated with saturated hydrogen chloride in diethyl ether and the white precipitate formed was collected by filtration to give the title compound (0.022 g, LRMS: 492.2).

Aufarbeitung

  1. concentrationThe reaction was then concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. custompassed through a fritted funnel
  4. additionThe filtrate was treated with saturated hydrogen chloride in diethyl ether
  5. customthe white precipitate formed
  6. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c4bdb46ab996423f929805ab86e19afc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

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