Hydrochloric Acid → (R,S)-[4-[2-(4-Fluorobenzoylamino)-4-oxo-4-(4-pyridin-4-ylpiperazin-1-yl)butyryl]-3-methoxycarbonylmethyl-2-oxopiperazin-1-yl]acetic Acid

HRID 1066573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066573
FC(F)(F)[C:3](O)=[O:4].[NH2:8][C@@H:9]([CH2:28][C:29](=[O:42])[N:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[C:14](=[O:22])[C@@:13]1([CH:25]=[C:26]=[O:27])OC)=[O:11].C(=O)([O-])O.[Na+].[F:48][C:49]1[CH:57]=[CH:56][C:52]([C:53](Cl)=[O:54])=[CH:51][CH:50]=1.Cl>O1CCOCC1.O>[F:48][C:49]1[CH:57]=[CH:56][C:52]([C:53]([NH:8][C@@H:9]([CH2:28][C:29](=[O:42])[N:30]2[CH2:31][CH2:32][N:33]([C:36]3[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=3)[CH2:34][CH2:35]2)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=[O:20])[C:14](=[O:22])[C@H:13]2[CH2:25][C:26]([O:4][CH3:3])=[O:27])=[O:11])=[O:54])=[CH:51][CH:50]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 86756995(r,s)-[4-[2-Amino-4-oxo-4-[4-(pyridin-4-yl)piperazin-1-yl]butyryl]-3-methoxy-carbonylmethyl-2-oxopiperazin-1-yl]acetic acid trifluoroacetic acid salt

Produkt 1

HCID 57122563(R,S)-[4-[2-(4-Fluorobenzoylamino)-4-oxo-4-(4-pyridin-4-ylpiperazin-1-yl)butyryl]-3-methoxycarbonylmethyl-2-oxopiperazin-1-yl]acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of (R,S)-[4-[2-amino-4-oxo-4-[4-(pyridin-4-yl)piperazin-1-yl]butyryl]-3-methoxy-carbonylmethyl-2-oxopiperazin-1-yl]acetic acid trifluoroacetic acid salt (0.25 g) produced in Working Example 21, an aqueous solution of sodium hydrogen carbonate (0.15 g), water (2.5 ml) and 1,4-dioxane (2.5 ml) was added 4-fluorobenzoyl chloride (0.051 ml) and the solution was stirred for 1 hour at room temperature. The pH of the reaction solution was adjusted to 3 with 1N hydrochloric acid and the solution was concentrated under reduced pressure. The concentrate was purified by means of CHP-20 column chromatography (eluent:H2O→15% acetonitrile aqueous solution→20% acetonitrile aqueous solution→25% acetonitrile aqueous solution→30% acetonitrile aqueous solution). The objected fraction was concentrated and subjected to lyophilization to give the titled compound (0.10 g) as a white amorphous powdery product.

Aufarbeitung

  1. customproduced in Working Example 21
  2. concentrationthe solution was concentrated under reduced pressure
  3. customThe concentrate was purified by means of CHP-20 column chromatography (eluent:H2O→15% acetonitrile aqueous solution→20% acetonitrile aqueous solution→25% acetonitrile aqueous solution→30% acetonitrile aqueous solution)
  4. concentrationThe objected fraction was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-51796c4b61304ba7a1b298e72ce66996
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242600B1

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