Diisopropylethylamine → Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate

HRID 348880

Reaktionsgleichung

Reaktionsgleichung von HRID 348880
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[CH:3]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH3:48][O:49][C:50](=[O:57])[CH2:51][CH2:52][C:53]([CH2:55][NH2:56])=[O:54]>C(Cl)Cl.CN(C=O)C>[CH3:48][O:49][C:50](=[O:57])[CH2:51][CH2:52][C:53](=[O:54])[CH2:55][NH:56][C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[C:1]([O:12][CH3:13])=[O:11])=[O:7]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 157921Methyl Aminolevulinate HydrochlorideHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 21086156Methyl 3-{[(5-methoxy-2,5-dioxopentyl)amino]carbonyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Methyl hydrogen isophthalate (1.8 g, 10.2 mmol) is dissolved in methylene chloride (10 mL) and DMF (10 mL), and diisopropylethylamine (4.4 mL, 25.5 mmol), HATU (4.6 g, 12.2 mmol), and 5-aminolevulinic acid methyl ester hydrochloride (2 g, 11.2 mmol) are added. The reaction stirred at room temperature 1 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 4% methanol/chloroform) provides the title compound. ESI MS m/z 306.1 [M−H]−.

Aufarbeitung

  1. customThe reaction is partitioned between ethyl acetate and water
  2. washThe organic layer is washed with 1 N hydrochloric acid, saturated sodium bicarbonate, and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 4% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-04e9b9a351e542c6ac111a020da63bef
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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