Ammonia → Carnosine

HRID 1815604Notes

Reaction equation

HRID 1815604 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C@@H:7]([CH2:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)[C:8]([OH:10])=[O:9])=[O:5])#[N:2].[Na].N>C(O)C.[Rh]>[CH:16]1[N:15]=[CH:14][NH:13][C:12]=1[CH2:11][C@H:7]([NH:6][C:4]([CH2:3][CH2:1][NH2:2])=[O:5])[C:8]([OH:10])=[O:9]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 178511198HCID 178511198, compound

Product 1

HCID 439224Carnosine

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

0.3 g of rhodium/activated carbon (5% Rh) was added to a solution of 1.90 g (7.8 mmol) of (S)-2-(cyanoacetylamino)-3-(1H-imidazol-4-yl)propionic acid, sodium salt (prepared according to Example 1) in 50 ml of ethanol/conc. ammonia solution (V:V=4:1). The mixture was hydrogenated at 110° C. and 45 bar for 1 h. This was followed by filtering off the catalyst and adjusting the filtrate to a pH of 8.2 with formic acid. After concentrating the solution under reduced pressure, the residue was suspended in 200 ml of ethanol and heated at 60° C. for 30 min. The product was filtered off, washed successively with ethanol, ethyl acetate and diethyl ether and finally dried.

Workup

  1. customwas hydrogenated at 110° C.
  2. filtrationby filtering off the catalyst
  3. concentrationAfter concentrating the solution under reduced pressure
  4. filtrationThe product was filtered off
  5. washwashed successively with ethanol, ethyl acetate and diethyl ether
  6. customfinally dried

Sources & evidence

ORD record
ord-ec33d6bd6cbc4fa9aabcab209c1e36cd
Source dataset
uspto-grants-2005_04
Patent number
US06878829B2

Reaction notes

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