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Potassium Phosphate, Tribasic → Methyl 7-amino-3a,4-dihydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate

HRID 595112
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 595112
[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([O:12][CH2:13][CH:14]2[CH:18]=[CH:17][CH2:16][NH:15]2)[C:5](Br)=[CH:4][CH:3]=1.N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]2[O:12][CH2:13][CH:14]3[CH:18]=[CH:17][CH2:16][N:15]3[C:5]2=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 86712821methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate2×

Produkt 1

HCID 86712820Methyl 7-amino-3a,4-dihydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylateAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of methyl 6-amino-3-bromo-2-(2,5-dihydro-1H-pyrrol-2-ylmethoxy)-benzoate (Intermediate 18, 1.64 g), copper (I) iodide (0.095 g), L-proline (0.115 g) and potassium phosphate tribasic (2.13 g) in anhydrous DMSO (10 mL) was evacuated and purged with nitrogen then heated to 90° C., under an atmosphere of nitrogen overnight. The resultant mixture was cooled and partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was extracted with more ethyl acetate. The combined organic layers were dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-30% to give methyl 7-amino-3a,4-dihydro-1H-benzo[b]pyrrolo[1,2-d][1,4]oxazine-6-carboxylate (0.370 g) as a brown oil.

Aufarbeitung

  1. customwas evacuated
  2. custompurged with nitrogen
  3. temperatureThe resultant mixture was cooled
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with more ethyl acetate
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by chromatography on silica
  11. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-30%

Quellen und Nachweise

ORD-Eintrag
ord-cefb70105238498b82902ae6fd028b02
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242997B2

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