Methanesulfonic Acid → Carnosine

HRID 2198677Notes

Reaction equation

HRID 2198677 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+:25](CCCC)(CCCC)CCCC)CCC.CS(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][NH2:25])=[O:18])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 4

HCID 6395Methanesulfonic AcidHCID 23040671,3-thiazinane-2,4-dioneHCID 2723671Tetrabutylammonium HydroxideHCID 178419078HCID 178419078, compound

Product 1

HCID 439224CarnosineYield 79.6%

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 were reacted, using 40% aqueous tetra-n-butylammonium hydroxide solution to raise pH and methanesulfonic acid to lower pH, to give 1.80 g. (79.6% yield) of L-carnosine.

Workup

  1. customto give 1.80 g

Sources & evidence

ORD record
ord-7cf1111d6d6d41fe879bb6ca67c8ac47
Source dataset
uspto-grants-1982_11
Patent number
US04359416

Reaction notes

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