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Diphenyl carbonate → phenyl 7-(dimethoxymethyl)-6-methoxy-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

HRID 1778043
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1778043
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][C:5]=1[O:14][CH3:15].[C:18]1([O:24][C:25](=O)[O:26]C2C=CC=CC=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[CH3:17][O:16][CH:3]([O:2][CH3:1])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][N:11]2[C:25]([O:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])=[CH:6][C:5]=1[O:14][CH3:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7597Diphenyl carbonateHCID 2733832Lithium hexamethyldisilazaneHCID 1180362517-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-methoxy-1,8-naphthyridine2×

Produkt 1

HCID 118036583phenyl 7-(dimethoxymethyl)-6-methoxy-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of 7-(dimethoxymethyl)-6-methoxy-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 309, 76 mg, 0.319 mmol) and diphenylcarbonate (137 mg, 0.638 mmol) in THF (2 ml) at −15° C. was treated drop wise with LHMDS (1 M in THF, 0.35 ml, 0.35 mmol) and stirred for 25 min. The reaction mixture was then quenched with sat. aq. NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100) to give the title compound as a yellow oil. (UPLC-MS 1) tR 0.93 min; ESI-MS 360.1 [M+H]+.

Aufarbeitung

  1. customThe reaction mixture was then quenched with sat. aq. NH4Cl
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100)

Quellen und Nachweise

ORD-Eintrag
ord-8c6b81481745444db36d412b01f72769
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266883B2

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