Hydrochloric Acid → Mirabegron

HRID 1392375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392375
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][CH2:12][C@@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[OH:14])=[CH:5][CH:4]=1.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([CH2:27][C:28](O)=[O:29])[N:26]=1.Cl.Cl.CN(C)CCCN=C=NCC.[OH-].[Na+]>O>[NH2:21][C:22]1[S:23][CH:24]=[C:25]([CH2:27][C:28]([NH:2][C:3]2[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][NH:11][CH2:12][C@H:13]([OH:14])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:7][CH:8]=2)=[O:29])[N:26]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 34665(2-Amino-1,3-thiazol-4-yl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 529530072-((4-Aminophenethyl)amino)-1-phenylethanol hydrochloride, (R)-

Produkt 1

HCID 9865528Mirabegron

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a mixed solution of 13.50 kg of (R)-2-[[2-(4-aminophenyl) ethyl]amino]-1-phenylethanol monohydrochloride, 7.29 kg of 2-aminothiazol-4-yl-acetic acid, 4.46 kg of concentrated hydrochloric acid and 270 L of water, 9.73 kg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride (EDC) was added at 15° C., and the mixture was stirred for one hour. A mixed solution of 4.10 kg of sodium hydroxide and 110 L of water was dropped in the reaction solution, thereby undergoing crystallization. A generated crystal was collected by filtration and washed with water to obtain 26.2 kg of a wet cake of the β-form crystal of (R)-2-(2-aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide. This crystal was used for recrystallization as it was in the wet state.

Aufarbeitung

  1. customcrystallization
  2. filtrationA generated crystal was collected by filtration
  3. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-7321fc6bd2354790823bd707d4a288b5
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342117B2

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