Benzenesulfonic Acid → Carnosine

HRID 2198678Notes

Reaction equation

HRID 2198678 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+:28](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C1(S(O)(=O)=O)C=CC=CC=1>C(OCC)(=O)C>[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][NH2:28])=[O:18])[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 7371Benzenesulfonic AcidHCID 23040671,3-thiazinane-2,4-dioneHCID 22149663HCID 22149663, compoundHCID 178419078HCID 178419078, compound

Product 1

HCID 439224Carnosine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Starting with 1.55 g. (10 mmol) of L-histidine, 2.62 g. (20 mmol) of tetrahydro-1,3-thiazin-2,4-dione, 40% methanolic benzyltri-n-butylammonium hydroxide solution to raise the pH benzenesulfonic acid to lower the pH and ethyl acetate as the crystallizing solvent, and following the procedure of Example 1, there is isolated L-carnosine in good yield.

Sources & evidence

ORD record
ord-3802275f4c724822b4bd6c393c01b762
Source dataset
uspto-grants-1982_11
Patent number
US04359416

Reaction notes

Loading…