Ammonia → Carnosine

HRID 1374133Notes

Reaction equation

HRID 1374133 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-(cyanoacetyl-amino)-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-536ab27b869e4a9a8b5bc4c5184bc730
Source dataset
uspto-grants-2007_01
Patent number
US07164028B2

Reaction notes

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