Anisole → D-Cysteinyl-L-proline acetate

HRID 262810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 262810
C([O:5][C:6](=[O:34])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:33])[C@@H:13]([CH2:22][S:23]CC1C=CC(OC)=CC=1)[NH:14]C(OC(C)(C)C)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)S(O)(=O)=O>ClCCl>[C:6]([OH:34])(=[O:5])[CH3:7].[NH2:14][C@@H:13]([C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:34])=[O:5])=[O:33])[CH2:22][SH:23]

Komponenten

5

Edukt 3

HCID 7519AnisoleHCID 62406Trifluoromethanesulfonic acidHCID 22805345N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester

Produkt 1

HCID 86736006D-Cysteinyl-L-proline acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester (1.8 g) and anisole (4.4 ml) in dichloromethane (8 ml) chilled in an ice bath, trifluoromethane sulfonic acid (6.0 g) is added. The ice bath is removed and the mixture is stirred at room temperature for thirty minutes. The dichloromethane is removed in vacuo and the residue is triturated with hexane (2×200 ml). The residue is dissolved in water and extracted twice with ether. The aqueous phase is applied to a column of 200 ml of cation exchange resin [Dowex 50] in the hydrogen cycle. The column is washed with water until no more acidic material is eluted. The D-cysteinyl-L-proline acetate is eluted with a pyridine-acetic acid buffer pH 6.5, yield 0.66 g. Rf =0.38 (silica gel, chloroform:methanol:acetic acid:water).

Aufarbeitung

  1. customThe ice bath is removed
  2. customThe dichloromethane is removed in vacuo
  3. customthe residue is triturated with hexane (2×200 ml)
  4. dissolutionThe residue is dissolved in water
  5. extractionextracted twice with ether
  6. washThe column is washed with water until no more acidic material
  7. washis eluted
  8. washThe D-cysteinyl-L-proline acetate is eluted with a pyridine-acetic acid buffer pH 6.5, yield 0.66 g

Quellen und Nachweise

ORD-Eintrag
ord-64f847bb8c0b45f593e61249b84d2ebe
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154960

Notizen zur Reaktion

Wird geladen…