Dicyclohexylcarbodiimide → N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester

HRID 261321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 261321
[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]([O:42][C:43]([NH:45][C@@H:46]([C:58](O)=[O:59])[CH2:47][S:48][CH2:49][C:50]1[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=1)=[O:44])([CH3:41])([CH3:40])[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:58](=[O:59])[C@@H:46]([CH2:47][S:48][CH2:49][C:50]1[CH:51]=[CH:52][C:53]([O:56][CH3:57])=[CH:54][CH:55]=1)[NH:45][C:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:44])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 6992555N-[(1,1-Dimethylethoxy)carbonyl]-S-[(4-methoxyphenyl)methyl]-D-cysteineHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 22805345N-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-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-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-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-tert-butyloxycarbonyl-S-p-methoxybenzyl-D-cysteinyl-L-proline tert-butyl ester as an oil. Rf =0.2 (silica gel, chloroform).

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-9623e251def24e199df1ae3c62230fe4
Quelldatensatz
uspto-grants-1979_08
Patentnummer
US04165320

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