Sodium Hydroxide → N-[Hydroxy(5-sulfanyl-3,4-dihydro-2H-pyrrol-2-yl)methylidene]cysteine

HRID 1656450Notes

Reaction equation

C[O:2][C:3](=[O:16])[C@H:4]([CH2:14][SH:15])[NH:5][C:6](=[O:13])[C@@H:7]1[CH2:11][CH2:10][C:9](=O)[NH:8]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1.[OH-].[Na+]>>[S:26]=[C:9]1[NH:8][C@H:7]([C:6]([NH:5][C@H:4]([C:3]([OH:2])=[O:16])[CH2:14][SH:15])=[O:13])[CH2:11][CH2:10]1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 87949Lawesson's reagent

HCID 22884206HCID 22884206, compound

Product 1

HCID 10220554N-[Hydroxy(5-sulfanyl-3,4-dihydro-2H-pyrrol-2-yl)methylidene]cysteine

Procedure

Thionation of N-(5-oxo-L-prolyl)-L-cysteine methyl ester with the Lawesson's reagent and the subsequent alkali hydrolysis with two sodium hydroxide equivalents in aqueous solution yields N-(5-thioxo-L-prolyl)-L-cysteine.

Sources & evidence

ORD record: ord-e21356afcaa548299cdfe4bb96e50da8
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254579

Reaction notes

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