Triethylamine → HCID 68978764, Verbindung

HRID 600277

Reaktionsgleichung

Reaktionsgleichung von HRID 600277
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[N:20]=[C:21]=[O:22].[NH2:23][C@@H:24]([C:29]([OH:31])=[O:30])[CH2:25]C(O)=O.C(N(CC)CC)C.C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)=[CH:4][C:3]=1[NH:20][C:21](=[O:22])[NH:23][CH:24]([CH3:25])[C:29]([OH:31])=[O:30]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 83887D-Aspartic AcidHCID 598565454-(4-Fluoro-3-isocyanato-benzyl)-2H-phthalazin-1-one

Produkt 1

HCID 68978764HCID 68978764, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 4-(3-isocyanato-benzyl)-2H-phthalazin-1-one (2)(1.4 g, 4.7 mmol) in dry DCM (40 ml) was added D-aspartic acid (0.455 g, 5.0 mmol), followed by triethylamine (1.4 ml, 10.0 mmol). The reaction was stirred at room temperature for 4 days. The reaction mixture was then filtered. The filtrate was then diluted with water (20 ml) and washed twice with DCM (2×20 ml). The combined DCM layers were dried over sodium sulfate and then concentrated in vacuo to afford a crude oil which was subjected to flash chromatography eluent neat ethyl acetate to remove impurity and the then 1:1 ethyl acetate/methanol to remove the desired component. (Rf of 0.2 in 1:1 ethyl acetate methanol). Single peak in LC-MS analysis, (0.79 g) requiring no further purification; m/z (LC-MS, ESP), RT=2.70 (M+H) 384;

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered
  2. additionThe filtrate was then diluted with water (20 ml)
  3. washwashed twice with DCM (2×20 ml)
  4. dry with materialThe combined DCM layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a crude oil which
  7. customto remove impurity
  8. customthe then 1:1 ethyl acetate/methanol to remove the desired component
  9. customno further purification
  10. customm/z (LC-MS, ESP), RT=2.70 (M+H) 384

Quellen und Nachweise

ORD-Eintrag
ord-e4cb7af33a5c4bd5a56a5f4010e4c443
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902193B2

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