2-Dimethylaminopyridine → 2-trimethylsilanyl-ethyl [(E)-9-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-9-oxo-non-6-enyl]-carbamate

HRID 1779226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779226
[CH:1]([C@H:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6](=[S:21])[NH:5]1)([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC.[CH3:43][Si:44]([CH3:63])([CH3:62])[CH2:45][CH2:46][O:47][C:48]([NH:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]/[CH:56]=[CH:57]/[CH2:58][C:59](O)=[O:60])=[O:49].P([O-])(O)(O)=O.[K+]>ClCCl>[CH:1]([C@H:4]1[C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:7][C:6](=[S:21])[N:5]1[C:59](=[O:60])[CH2:58]/[CH:57]=[CH:56]/[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][NH:50][C:48](=[O:49])[O:47][CH2:46][CH2:45][Si:44]([CH3:43])([CH3:63])[CH3:62])([CH3:3])[CH3:2]

Komponenten

7

Edukt 5

HCID 218852-DimethylaminopyridineHCID 516951Monobasic potassium phosphateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 39058337(S)-4-Isopropyl-5,5-diphenyloxazolidine-2-thioneHCID 90060233(E)-9-(2-trimethylsilanyl-ethoxycarbonylamino)-non-3-enoic acid

Produkt 1

HCID 900602442-trimethylsilanyl-ethyl [(E)-9-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-9-oxo-non-6-enyl]-carbamateAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-4-Isopropyl-5,5-diphenyl-oxazolidine-2-thione (2.3 g, 8.28 mmol) was suspended in dichloromethane (17.5 mL), and the mixture was then cooled to 0° C. in an ice bath. Dimethylaminopyridine (97 mg, 0.794 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.00 g, 10.4 mmol) were added and the mixture was then stirred for 25 minutes. To this suspension was added a solution of (E)-9-(2-trimethylsilanyl-ethoxycarbonylamino)-non-3-enoic acid (2.50 g, 7.92 mmol) in dichloromethane (17.5 mL). After stirring at 0° C. for 7.5 hours, an aqueous solution (50 mL) of 10% potassium dihydrogen phosphate and dichloromethane (40 mL) were added and the mixture was separated. The organic layer was washed with a saturated aqueous solution (40 mL) of sodium chloride, then dried over anhydrous sodium sulfate, and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 3.01 g (5.06 mmol, yield 64%) of 2-trimethylsilanyl-ethyl [(E)-9-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-9-oxo-non-6-enyl]-carbamate.

Aufarbeitung

  1. stirringAfter stirring at 0° C. for 7.5 hours
  2. customthe mixture was separated
  3. washThe organic layer was washed with a saturated aqueous solution (40 mL) of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0ed038e37559455c8fe1cf6a718e50a1
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266853B2

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