Reaktion #975403

Reaktionsgleichung

3-phenyl-5-piperazino-1,2,4-thiadiazole

pentafluorophenyl (2S)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate

pentafluorophenyl (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate

(2S,3S)-N,2-dihydroxy-5-methyl-3-{[4-(2-pyridinyl)-1-piperazinyl]carbonyl}hexanamide

Intermediate 1

(2S,3S)-N,2-dihydroxy-5-methyl-3-{[4-(2-pyridinyl)-1-piperazinyl]carbonyl}hexanamide

HCl

→

title product

Ausbeute 5.8%

(5S)-2,2-dimethyl-5-((1S)-3-methyl-1-{[4-(3-phenyl-1,2,4-thiadiazol-5-yl)-1-piperazinyl]carbonyl}butyl)-1,3-dioxolan-4-one

Ausbeute 5.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting reaction mixture
2. 2
   Extraktionthe resulting mixture was extracted with EtOAc
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto give an oil
7. 7
   FiltrationThe precipitate was filtered off
8. 8
   Sonstigethe mother liquids were evaporated
9. 9
   Sonstigethe resulting residue was then purified by chromatography (SiO2, gradient from 2/1 to 1/1 c-hex/EtOAc in about 30 min)

Vorschrift

To a solution of a 55/45 diastereoisomeric mixture of pentafluorophenyl (2S)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate and pentafluorophenyl (2R)-2-[(4S)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]-4-methylpentanoate (Intermediate 1; 150.0 mg; 0.38 mmol; 1.0 eq.) in DMF (1.5 mL) was added 3-phenyl-5-piperazino-1,2,4-thiadiazole (93.2 mg; 0.38 mmol; 1.0 eq.) and the resulting reaction mixture was stirred at RT for 14 h. An aqueous solution of HCl (1N) was added and the resulting mixture was extracted with EtOAc, dried over MgSO4, filtered and evaporated to give an oil. This residue was taken up in CD3OD. The precipitate was filtered off and the mother liquids were evaporated and the resulting residue was then purified by chromatography (SiO2, gradient from 2/1 to 1/1 c-hex/EtOAc in about 30 min) to give the title product as a colorless oil (10 mg; 5.8%). M+(ESI): 459.0. HPLC (Condition A): Rt: 4.5 min (HPLC purity: 98.5%).

Quelle