3-Pyridineacetic acid → N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester

HRID 1291765

Reaktionsgleichung

Reaktionsgleichung von HRID 1291765
[C:1]([O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:11])[CH3:10])[NH2:8])([CH3:4])([CH3:3])[CH3:2].Cl.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21](O)=[O:22])[CH:15]=1.C(OP(C#N)(=O)OCC)C>CN(C=O)C.C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:12])[C@H:7]([CH:9]([CH3:10])[CH3:11])[NH:8][C:21](=[O:22])[CH2:20][C:16]1[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 1083-Pyridineacetic acidHCID 313Hydrochloric AcidHCID 76257Diethyl cyanophosphonateHCID 114626tert-Butyl L-valinate

Produkt 1

HCID 18659858N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4.2 ml of triethylamine are added dropwise at 0° to a solution of 3.36 g (16 mmol) of (L)-valine-tert-butyl ester.HCl, 2 g (14.5 mmol) of 3-pyridylacetic acid and 2.17 ml (14.3 mmol) of cyanophosphonic acid diethyl ester in 20 ml of DMF. The reaction mixture is stirred for 48 h at RT, and then diluted with methylene chloride and washed with 10% citric acid as well as saturated sodium hydrogen carbonate solution. The organic phase is filtered through cotton wadding and, after removal of the solvent by evaporation, yields N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester, which is directly further used in a).

Aufarbeitung

  1. washwashed with 10% citric acid as well as saturated sodium hydrogen carbonate solution
  2. filtrationThe organic phase is filtered through cotton wadding
  3. customafter removal of the solvent
  4. customby evaporation

Quellen und Nachweise

ORD-Eintrag
ord-84fe4bba081d417da4fd906a950e4952
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753652

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