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2-Dimethylaminopyridine → (E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one

HRID 1779234
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1779234
[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.[C:43]1([CH2:49][CH2:50][CH2:51][CH2:52][C:53]2([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]/[CH:64]=[CH:65]/[CH2:66][C:67](O)=[O:68])[O:57][CH2:56][CH2:55][O:54]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.P([O-])(O)(O)=O.[Na+]>ClCCl.C(OCC)(=O)C>[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:67](=[O:68])[CH2:66]/[CH:65]=[CH:64]/[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59][CH2:58][C:53]1([CH2:52][CH2:51][CH2:50][CH2:49][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[O:57][CH2:56][CH2:55][O:54]1)([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23672064Monosodium phosphateHCID 39058337(S)-4-Isopropyl-5,5-diphenyloxazolidine-2-thioneHCID 90060189(E)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-enoic acid

Produkt 1

HCID 90060381
(E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one
Ausbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-4-Isopropyl-5,5-diphenyl-oxazolidine-2-thione (412 mg, 1.39 mmol) was suspended in dichloromethane (3.3 mL), and then cooled to 0° C. in an ice bath. Dimethylaminopyridine (16 mg, 0.131 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (315 mg, 1.64 mmol) were added in this order. A solution of a commercially available reagent of (E)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-enoic acid (476 mg, 1.27 mmol) in dichloromethane (3.4 mL) was then added. After stirring at 0° C. for 2 hours, an aqueous solution (50 mL) of 10% sodium dihydrogen phosphate and ethyl acetate (50 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 445 mg (0.681 mmol, 54% yield) of (E)-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-10-[2-(4-phenyl-butyl)-[1,3]dioxolan-2-yl]-dec-3-en-1-one (ESI (LC/MS positive mode) m/z 654 (M+H); Rt 3.07 min.).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ac3c38e6f91e4aa2bfb295a09459d534
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266853B2

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