Diphosgene → HCID 67502941, Verbindung

HRID 1887195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887195
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]([NH:8][C:9]([C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:10])[CH2:6][CH3:7].Cl[C:20](OC(Cl)(Cl)Cl)=[O:21]>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]([N:8]1[C:9](=[O:10])[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:16]=2[NH:17][C:20]1=[O:21])[CH2:6][CH3:7]

Komponenten

5

Edukt 2

HCID 10426DiphosgeneHCID 67501919(R)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester

Produkt 1

HCID 67502941HCID 67502941, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 1.6 g of (R)-3-[(3-amino-pyridine-2-carbonyl)-amino]-pentanoic acid methyl ester and 0.86 mL of trichloromethyl chloroformate in 25 mL of tetrahydrofuran is stirred at 90° C. for 3 h. The resulting mixture is diluted with saturated sodium bicarbonate solution and the product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography on silica to give 1.75 g (99%) of (R)-3-(2,4-dioxo-1,4-dihydro-2H-pyrido[3,2-d]pyrimidin-3-yl)-pentanoic acid methyl ester.

Aufarbeitung

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-1a1fb61c63ec4bb7b34e2fcc42f82af5
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501749B2

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