Diisopropylethylamine → HCID 69376816, Verbindung

HRID 852251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852251
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.Cl[C:23]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][N:24]=1.CCN(C(C)C)C(C)C>C(OCCO)C>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:23]2[C:32]3[C:27](=[CH:28][N:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][N:24]=2)=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl esterHCID 128847741-Chloro-2,6-naphthyridine

Produkt 1

HCID 69376816HCID 69376816, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8076Glycol monoethyl etherLösungsmittel

Versuchsvorschrift

(S)-3-(4-Amino-phenyl)-2-tert-butoxycarbonylamino propionic acid methyl ester (574 mg, 1.95 mmol), 1-Chloro-2,6-naphthyridine (350 mg, 2.13 mmol) (prepared according to the method of Van der Plas, H. C. et al J. Heterocyclic Chem. 1981, 18, 1349) and DIPEA (372 μl, 2.13 mmol) in 2-ethoxyethanol (0.5 ml) were stirred at 130° C. under N2 overnight. The reaction mixture was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3 (30 ml). The phases were separated and the aqueous layer re-extracted with EtOAc (3×30 ml). The combined organic extracts were dried (MgSO4) and the solvents eliminated in vacuo. The residue was purified by flash chromatography (5:1 to 1:1 hexanes/EtOAc) to give (S)-2-tert-butoxycarbonylamino-3-[4-([2,6]naphthyridin-1-ylamino)phenyl] propionic acid methyl ester (385 mg, 47%) as an orange foam.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc (70 ml) and saturated aqueous NaHCO3 (30 ml)
  2. customThe phases were separated
  3. extractionthe aqueous layer re-extracted with EtOAc (3×30 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customThe residue was purified by flash chromatography (5:1 to 1:1 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7970129eae984432b7ee9dc187f7233c
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253171B2

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