Dicyclohexylcarbodiimide → N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester

HRID 2308785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2308785
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]([NH:41][CH:42]([C:48](O)=[O:49])[CH2:43][S:44][C:45](=[O:47])[CH3:46])(=[O:40])[CH3:39]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:48](=[O:49])[CH:42]([CH2:43][S:44][C:45](=[O:47])[CH3:46])[NH:41][C:38](=[O:40])[CH3:39])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 4321391HCID 4321391, VerbindungHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 14181603N,S-Diacetyl-DL-cysteinyl-L-proline tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of L-proline tert-butyl ester (0.85 g.) and hydroxybenzotriazole (0.67 g.) in methylene chloride (10 ml.) chilled in an ice bath, dicyclohexylcarbodiimide (1.03 g.) and N,S-diacetyl-D,L-cysteine (1.7 g.) are added in that order. After fifteen minutes, the ice bath is removed and the mixture is stirred at room temperature overnight. The precipitate is filtered off and the filtrate is washed with 10% potassium bisulfate, water, saturated sodium bicarbonate, and water. The organic phase is dried and concentrated to dryness in vacuo to give N,S-diacetyl-D,L-cysteinyl-L-proline tert-butyl ester as an oil. Rf =0.25 (silica gel, ethylacetate).

Aufarbeitung

  1. waitAfter fifteen minutes
  2. customthe ice bath is removed
  3. filtrationThe precipitate is filtered off
  4. washthe filtrate is washed with 10% potassium bisulfate, water, saturated sodium bicarbonate, and water
  5. customThe organic phase is dried
  6. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2e0d699b036240a18e39d792dcb73a6d
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04690936

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