1,2-Dichloroethane → (R)-Methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)piperidine-2-carboxylate

HRID 2403506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2403506
[C:1]([O:9][C:10]1[C:18]([O:19][CH3:20])=[CH:17][C:13]([C:14]([OH:16])=O)=[C:12]([N+:21]([O-:23])=[O:22])[CH:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[C:30]([O:32][CH3:33])=[O:31].C(Cl)CCl.CCN(C(C)C)C(C)C>CC(N(C)C)=O>[CH2:1]([O:9][C:10]1[C:18]([O:19][CH3:20])=[CH:17][C:13]([C:14]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]2[C:30]([O:32][CH3:33])=[O:31])=[O:16])=[C:12]([N+:21]([O-:23])=[O:22])[CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 7408456methyl (R)-piperidine-2-carboxylateHCID 594400844-Benzoyloxy-5-methoxy-2-nitro benzoic acid

Produkt 1

HCID 86644085(R)-Methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)piperidine-2-carboxylateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

4-(benzoyloxy)-5-methoxy-2-nitrobenzoic acid (1.70 g, 5.61 mmol), (R)-methyl piperidine-2-carboxylate (1.05 g, 5.84 mmol), EDC (3.90 g, 20.31 mmo) and DIPEA (1.0 ml, 5.75 mmol) was stirred in 20 ml of DMA over night. The mixture was evaporated, diluted with DCM, washed with washed 1M NaH2PO4/NaCl (conc) and 0.1 M NaHCO3/NaCl (conc) separately. The organic solvent layer was separated and dried over MgSO4, filtered, concentrated and purified on SiO2 chromatography eluted with EtAc/DCM (1:15) to afford 1.772 g (74%) of the title product. 1H NMR (CDCl3) 7.69 (s, 1H), 7.40-7.38 (m, 2H), 7.35-7.27 (m, 3H), 6.76 (d, 1H), 5.15 (s, 2H), 3.91 (s, 3H), 3.83 (s, 1H), 3.73 (s, 3H), 3.18 (m, 2H), 1.70 (m 2H), 1.47 (m, 4H); 13C NMR 171.89, 171.33, 155.10, 154.78, 148.32, 135.59, 129.05, 128.74, 127.80, 109.66, 109.58, 109.41, 71.63, 56.92, 52.70, 52.19, 45.70, 39.92, 27.29, 26.35, 21.63; MS m/z+451.2 (M+Na).

Aufarbeitung

  1. customThe mixture was evaporated
  2. additiondiluted with DCM
  3. washwashed
  4. washwith washed 1M NaH2PO4/NaCl (conc) and 0.1 M NaHCO3/NaCl (conc) separately
  5. customThe organic solvent layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on SiO2 chromatography
  10. washeluted with EtAc/DCM (1:15)

Quellen und Nachweise

ORD-Eintrag
ord-6120088afc8b45f48cf691ced0b92b7e
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802667B2

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