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1,2-Dichloroethane → tert-Butyl 5-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)isoindoline-2-carboxylate

HRID 710469
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 710469
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([OH:9])=O)[CH3:2].O[NH:17][C:18]([C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23]2)=[NH:19].C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[O:9][N:17]=[C:18]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23]4)[N:19]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]
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Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 794173,4-Diethoxybenzoic acidHCID 178451481HCID 178451481, Verbindung

Produkt 1

HCID 86661809tert-Butyl 5-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)isoindoline-2-carboxylateAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3,4-diethoxybenzoic acid (0.19 g; 0.904 mmol), a product of Step D (0.25 g; 0.904 mmol) and EDC (0.27 g; 1.4 mmol) in anhydrous DMF (2 ml) was stirred at ˜60° C. for 1 h, then cooled to room temperature and diluted to 20 ml with EtOAc. This was washed with H2O (2×5 ml), brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness. The residue was diluted to 3 ml with anhydrous diglyme and 1M TBAF in THF (0.5 ml) was added and the resulting mixture was stirred at ˜80° C. for 1 h, then solvents were removed in vacuo. The residue was purified by crystallization from MeOH, to give the title compound (0.084 g; 20%) as greyish solid. 1H-NMR (CDCl3) 1.4-1.6 (m, 15H+H2O); 4.14-4.24 (m, 4H); 4.7-4.76 (m, 4H); 6.97 (d, 1H, J=6 Hz); 7.32-7.4 (m, 1H); 7.66 (d, 1H, J=3 Hz); 7.78 (dd, 1H, J=3, 9 Hz); 8.02-8.08 (m, 2H).

Aufarbeitung

  1. washThis was washed with H2O (2×5 ml), brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customfiltrate evaporated to dryness
  5. additionThe residue was diluted to 3 ml with anhydrous diglyme and 1M TBAF in THF (0.5 ml)
  6. additionwas added
  7. customsolvents were removed in vacuo
  8. customThe residue was purified by crystallization from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-f98aa3ddcb494a7eb53b3bb55670ee16
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181182B2

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