Sodium Hydroxide → HCID 54110235, Verbindung

HRID 47047

Reaktionsgleichung

Reaktionsgleichung von HRID 47047
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].[OH-].[Na+].[CH:19]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:25]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:26])[CH3:3]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 70602162L-alanyl-L-proline ethylamide hydrobromide

Produkt 1

HCID 54110235HCID 54110235, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1.25 g (0.00425 mol) of L-alanyl-L-proline ethylamide hydrobromide were suspended in 20 ml of dichloromethane and to the suspension were added 17.84 ml (0.00892 mol) of 0.5-N sodium hydroxide solution followed by 0.62 ml (1.1 equivalents) of cyclohexane carboxylic acid chloride. The mixture was stirred vigorously for 1 hour. The solution was diluted with 80 ml of dichloromethane, the organic layer was separated, washed with 60 ml of brine, dried over magnesium sulphate and evaporated to give a solid. Recrystallisation from ethyl acetate yielded 0.83 g (60%) of N-cyclohexylcarbonyl-L-alanyl-L-proline ethylamide of melting point 190.5°-191.5° C.; [α]D20 =-116.0° (c=1.055% in methanol).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with 60 ml of brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customto give a solid
  6. customRecrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ee71e4b6f4b54c56a0a6aad5f6d89a52
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04176116

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