Acetone → Potassium 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylate

HRID 1948335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1948335
[OH-].[K+:2].[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][N:24]=2)[CH2:16][C@@H:15]1[F:28])=[O:12].CC(C)=O>CO.CC(C)=O.O>[Cl:3][C:4]1[C:8]([Cl:9])=[C:7]([CH3:10])[NH:6][C:5]=1[C:11]([NH:13][C@@H:14]1[CH2:19][CH2:18][N:17]([C:20]2[S:21][C:22]([C:25]([O-:27])=[O:26])=[CH:23][N:24]=2)[CH2:16][C@@H:15]1[F:28])=[O:12].[K+:2]

Komponenten

6

Edukt 3

HCID 180Acetone2×HCID 14797Potassium HydroxideHCID 117187292-[(3s,4r)-4-{[(3,4-Dichloro-5-Methyl-1h-Pyrrol-2-Yl)carbonyl]amino}-3-Fluoropiperidin-1-Yl]-1,3-Thiazole-5-Carboxylic Acid

Produkt 1

HCID 68515353Potassium 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 18366337Propan-2-one--water (1/1)Lösungsmittel

Versuchsvorschrift

An aqueous solution of potassium hydroxide (0.1 M, 4.75 ml, 0.475 mmol) was added to a solution of 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-1,3-thiazole-5-carboxylic acid (Example 42, 200 mg, 0.475 mmol) in methanol (35 ml). The mixture was stirred for 1 h and then concentrated under reduced pressure to provide the crude salt (230 mg). The salt was dissolved in acetone/water (50 ml; 48:2) and acetone was added slowly to the stirred mixture until it became cloudy. Stirring was continued and more acetone was added very slowly over 20 min. The mixture was stored at 4° C. overnight. The solid was collected by filtration and air dried for 24 h to provide the salt (160 mg).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customto provide the crude salt (230 mg)
  3. stirringStirring
  4. waitThe mixture was stored at 4° C. overnight
  5. filtrationThe solid was collected by filtration and air
  6. customdried for 24 h

Quellen und Nachweise

ORD-Eintrag
ord-78766b359163470f9c65639907fa12ce
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399489B2

Notizen zur Reaktion

Wird geladen…