Reaktion #1783101

Reaktionsgleichung

3,3-Dimethylbutan-1-amine

2-(4-tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde

(S)-2-mercaptosuccinic acid

→

2-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

Ausbeute 27.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux overnight with a Dean-Stark trap
3. 3
   EinengenThe reaction mixture was concentrated to a brown oil
4. 4
   workup.DISSOLUTIONThis oil was redissolved in toluene
5. 5
   Einengen, concentrated to an oil
6. 6
   Sonstigetriturated with ether
7. 7
   Sonstigeto give a beige solid, which
8. 8
   Filtrationwas filtered off
9. 9
   Sonstigedried

Vorschrift

3,3-Dimethylbutan-1-amine (0.7 g, 6.8 mmol) and 2-(4-tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde (0.96 g, 3.4 mmol) were combined in toluene and heated to reflux overnight with a Dean-Stark trap attached. The reaction mixture was concentrated to a brown oil. This oil was redissolved in toluene and (S)-2-mercaptosuccinic acid (510 mg, 3.4 mmol) was added. The reaction mixture was heated at 80° C. for 16 hrs., concentrated to an oil, and triturated with ether to give a beige solid, which was filtered off and dried to give 2-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (0.45 g, 0.92 mmol, 27% yield) as a solid. LC/MS MH+ 498.45.

Quelle