Diclofenac → HCID 178520231, compound

HRID 1611406Notes

Reaction equation

HRID 1611406 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([NH:11][C:12]2[C:13]([Cl:19])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])=[C:5]([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:32][C@H:33]([C:40]([OH:42])=[O:41])[CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1>>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[NH:11][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH2:7][C:8]([O:10][NH:32][C@H:33]([C:40]([OH:42])=[O:41])[CH2:34][C:35]1[N:39]=[CH:38][NH:37][CH:36]=1)=[O:9]

Participants

4

Reactant 3

HCID 3033DiclofenacHCID 682631,1'-CarbonyldiimidazoleHCID 178419078HCID 178419078, compound

Product 1

HCID 178520231HCID 178520231, compound

Procedure

To a diclofenac solution (3 g, 10.13 mmoles) in tetrahydrofuan (50 ml) cooled at 0° C., 1,1′-carbonyldiimidazol (1.69 g, 10.13 mmoles) is added under stirring. After 10 minutes the solution is treated with (L) histidine (1.57 g, 10.13 mmoles) and left under stirring at room temperature for 4 hours. The reaction mixture is concentrated under vacuum, treated with methylene chloride and then washed in sequence with HCl 1% and then with water. The organic phase is anhydrified with sodium sulphate and evaporated under vacuum. The obtained residue is purified by chromatography on silica gel column, eluting with ethyl acetate. [2-[(2,6-dichlorophenyl)amino]benzeneacetyloxy](L)-histidine is obtained.

Workup

  1. waitleft
  2. stirringunder stirring at room temperature for 4 hours
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. additiontreated with methylene chloride
  5. washwashed in sequence with HCl 1%
  6. customevaporated under vacuum
  7. customThe obtained residue is purified by chromatography on silica gel column
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-13af9737254844d892c52075f8c756db
Source dataset
uspto-grants-2006_01
Patent number
US06987120B1

Reaction notes

Loading…