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Water → Methyl 7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)-3-hydroxyheptanoate

HRID 517917
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 517917
[C:1]1([CH3:35])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]4[O:32]N=[C:30]([O:33][CH3:34])[CH2:29]4)[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.B(O)(O)O.[OH2:40]>CO>[C:1]1([CH3:35])[CH:2]=[CH:3][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([OH:32])[CH2:29][C:30]([O:33][CH3:34])=[O:40])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 7628Boric AcidHCID 896900075-(4-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-3-methoxy-4,5-dihydroisoxazole

Produkt 1

HCID 89689978Methyl 7-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)-3-hydroxyheptanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Versuchsvorschrift

A solution of 5-(4-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-3-methoxy-4,5-dihydroisoxazole (step 2) (94 mg, 0.2 mmol) in MeOH (3 ml) and water (0.2 ml) was treated with boric acid (37.1 mg, 0.600 mmol) followed by Mo(CO)6 (37.0 mg, 0.140 mmol). The resulting mixture was heated at overnight. After cooling to RT, the mixture was concentrated under reduced pressure and diluted with DCM. The organic portion was washed with water and dried by passing through a phase separating column. The solvent was removed under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-60% EtOAc in iso-hexane afforded the titled compound;

Aufarbeitung

  1. temperatureThe resulting mixture was heated at overnight
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additiondiluted with DCM
  4. washThe organic portion was washed with water
  5. customdried
  6. customseparating column
  7. customThe solvent was removed under reduced pressure and purification of the crude product by chromatography on silica eluting with 0-60% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-72cd4915551541a4ae0d6468ee02476f
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09115129B2

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