S-benzyl-L-cysteine → N-carbamyl-S-benzylcysteine

HRID 964041

Reaktionsgleichung

Reaktionsgleichung von HRID 964041
[CH2:1]([S:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:15][C:16]#[N:17].[K+]>>[C:16]([NH:11][C@H:10]([C:12]([OH:14])=[O:13])[CH2:9][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:15])[NH2:17]

Komponenten

3

Edukt 2

HCID 193613S-benzyl-L-cysteineHCID 11378442Potassium cyanate

Produkt 1

HCID 57148047N-carbamyl-S-benzylcysteine

Versuchsvorschrift

The desired compound was synthesized from S-benzyl-L-cysteine (2 g, 9.48 mmol) (Fluka) and potassium cyanate (1.7 g, 21 mmol) by a modification of published protocols [see Coll. Czech Chem. Commun. 33:2918 (1968)]. Instead of isolating the N-carbamyl-S-benzylcysteine intermediate, after an initial reflux of 1 h, 25 ml of 10% hydrochloric acid was added and reflux was continued for 1.5 h. Upon cooling, the desired product precipitated as a white solid 1.7 g (77% yield), melting point 119.5°-120.5° C.

Quellen und Nachweise

ORD-Eintrag
ord-c6bdfad1771c4459b3c1bd5e0e7d25e7
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05767140

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