Trifluoroacetic acid methylene chloride → (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

HRID 1795020

Reaktionsgleichung

Reaktionsgleichung von HRID 1795020
[OH:1][C@@H:2]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([CH3:27])=[N:24][C:23]=2[CH:28]=1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1.FC(F)(F)C(O)=O.C(Cl)Cl>CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>[CH3:27][C:25]1[S:26][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][C@H:2]([OH:1])[CH2:3][N:4]3[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]3)=[CH:28][C:23]=2[N:24]=1

Komponenten

5

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 29943209tert-butyl 4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinecarboxylate

Produkt 1

HCID 29943216(2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperazinecarboxylate, a compound of formula (5) (2.0 g, 4.9 mmol), and 25% trifluoroacetic acid/methylene chloride (20 ml) was allowed to stir at room temperature overnight. The solvent was evaporated (in vacuo) to yield an oil. The oil was diluted with acetone (20 ml) and solid potassium carbonate was added until the foaming stopped. The resulting mixture was allowed to stir overnight. The solution was filtered through Celite 512, and the filtrate was evaporated (in vacuo), to yield an oil. The oil was placed under high vacuum overnight, to yield (2R)-1-(2-methylbenzothiazol-5-yloxy)-3-piperazinylpropan-2-ol as a clear viscous oil (3.4 g. 6.3 mmol).

Aufarbeitung

  1. customThe solvent was evaporated (in vacuo)
  2. customto yield an oil
  3. additionwas added until the foaming
  4. stirringto stir overnight
  5. filtrationThe solution was filtered through Celite 512
  6. customthe filtrate was evaporated (in vacuo)
  7. customto yield an oil
  8. customwas placed under high vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-5e36fde42d4146d4b3529bb9ed652be8
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026321B2

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