Reaktion #975409

Reaktionsgleichung

Water

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

(3S)-3-methyl-1-pyridin-2-ylpiperazine

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

Intermediate 4

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

→

title compound

Ausbeute 22.0%

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

Ausbeute 22.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting reaction mixture
2. 2
   Extraktionthe mixture was extracted with Et2O
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give an oil
8. 8
   SonstigePurification by chromatography (SiO2, gradient from 10% EtOAc in c-hex up to 40% EtOAc in c-hex in 15 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, 198 mg; 0.50 mmol; 1.0 eq.) in DMF (4 mL) was added (3S)-3-methyl-1-pyridin-2-ylpiperazine (Intermediate 4, 88.6 mg; 0.50 mmol; 1.0 eq.) and the resulting reaction mixture was stirred 48 h at RT. Water was added and the mixture was extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give an oil. Purification by chromatography (SiO2, gradient from 10% EtOAc in c-hex up to 40% EtOAc in c-hex in 15 min) gave the title compound as a colorless oil (43 mg; 22%) (mixture of 2 diastereoisomers). M+(ESI): 390.3.

Quelle