Dimethylformamide → N-carbobenzyloxy-cis-4-(1-adamantyl)-L-proline, methyl ester

HRID 1447456

Reaktionsgleichung

Reaktionsgleichung von HRID 1447456
[C:1]12(O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CN(C)C=O.[H-].[Na+].[C:19]([N:29]1[CH2:37][C@H:36](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:35][C@H:30]1[C:31]([O:33][CH3:34])=[O:32])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C1C=CC=CC=1>[C:19]([N:29]1[CH2:37][C@@H:36]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)[CH2:35][C@H:30]1[C:31]([O:33][CH3:34])=[O:32])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 641521-AdamantanolHCID 391525Zofenopril Impurity 4

Produkt 1

HCID 131712676N-carbobenzyloxy-cis-4-(1-adamantyl)-L-proline, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 5.3 g. (0.035 mole) of 1-adamantanol in 40 ml. of dimethylformamide and 80 ml. of benzene is treated with 1.6 g. of sodium hydride (50% dispersion in mineral oil). The mixture is refluxed for 15 minutes, cooled, and treated with 7.5 g. (0.017 mole) of N-carbobenzyloxy-trans-4-tosyloxy-L-proline, methyl ester. The resulting reaction mixture is stirred and refluxed for four hours, cooled, and the solvent removed under reduced pressure. The residue is dissolved in 100 ml. of chloroform and then washed with 25 ml. of water (3 times). The organic phase is dried (MgSO4), filtered, and the solvent evaporated to give N-carbobenzyloxy-cis-4-(1-adamantyl)-L-proline, methyl ester.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 15 minutes
  2. temperaturecooled
  3. additiontreated with 7.5 g
  4. customThe resulting reaction mixture
  5. temperaturerefluxed for four hours
  6. temperaturecooled
  7. customthe solvent removed under reduced pressure
  8. dissolutionThe residue is dissolved in 100 ml
  9. washof chloroform and then washed with 25 ml
  10. dry with materialThe organic phase is dried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-17a85010cd0443cb8da868275f7c2514
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04316906

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