3-Nitrobenzoic acid → Carnosine

HRID 2198679Notes

Reaction equation

HRID 2198679 reaction equation
[NH2:1][C@H:2]([C:9]([OH:11])=[O:10])[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.S1[CH2:17][CH2:16][C:15](=[O:18])NC1=O.[OH-].C[N+:22](C)(C)C.[N+](C1C=C(C=CC=1)C(O)=O)([O-])=O>>[CH:5]1[N:6]=[CH:7][NH:8][C:4]=1[CH2:3][C@H:2]([NH:1][C:15]([CH2:16][CH2:17][NH2:22])=[O:18])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 4

HCID 84973-Nitrobenzoic acidHCID 60966Tetramethylammonium hydroxideHCID 23040671,3-thiazinane-2,4-dioneHCID 178419078HCID 178419078, compound

Product 1

HCID 439224Carnosine

Procedure

Following the procedure of Example 1, 1.55 g. (10 mmol) of L-histidine and 2.62 g. (20 mmol) of tetrahydro-1,3-thiazin-2,4-dione are reacted, using 40% aqueous tetramethylammonium hydroxide solution to raise pH and m-nitrobenzoic acid to lower pH, to give L-carnosine in good yield.

Sources & evidence

ORD record
ord-d96d20c8a1134f2a9462773eee4b1b94
Source dataset
uspto-grants-1982_11
Patent number
US04359416

Reaction notes

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