Triethylamine → HCID 178520532, compound

HRID 2224035Notes

Reaction equation

HRID 2224035 reaction equation
[CH:1]1[N:5]=[CH:4][NH:3][C:2]=1[CH2:6][C@H:7]([NH:11][C:12]([CH2:14][CH2:15][NH2:16])=[O:13])[C:8]([OH:10])=[O:9].C(N(CC)CC)C.[Br:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>CN(C)C=O.C(OCC)(=O)C>[Br:24][CH2:25][CH2:26][CH2:27][C:28]([NH:16][CH2:15][CH2:14][C:12]([NH:11][C@H:7]([C:8]([OH:10])=[O:9])[CH2:6][C:2]1[N:3]=[CH:4][NH:5][CH:1]=1)=[O:13])=[O:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 702254-Bromobutyryl chlorideHCID 439224Carnosine

Product 1

HCID 178520532HCID 178520532, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of carnosine (5 g, 22.1 mmoles) in N,N-dimethylformamide (80 ml), triethylamine (4.62 ml, 33.1 mmoles) and 4-bromobutyrylchloride (chloride of 4-bromobutyric acid-83.85 ml, 33.1 mmoles) are added. The solution is left under stirring for 24 hours at room temperature, then it is diluted with ethyl acetate and the organic phase is washed with water. The organic phase is then anhydrified with sodium sulphate and evaporated at reduced pressure. The obtained crude product is purified by chromatography on silica gel eluting with ethyl acetate, obtaining the final product.

Workup

  1. waitThe solution is left
  2. washthe organic phase is washed with water
  3. customevaporated at reduced pressure
  4. customThe obtained crude product
  5. customis purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-72acd6f540b4404ebdc0d95ec4da2aa3
Source dataset
uspto-grants-2008_05
Patent number
US07378412B2

Reaction notes

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