Diclofenac → HCID 178520231, compound

HRID 749223Notes

Reaction equation

HRID 749223 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>O1CCCC1>[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

5

Reactant 3

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

Product 1

HCID 178520231HCID 178520231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a diclofenac solution (3 g, 10.13 mmoles) in tetrahydrofuran (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-e29f1ab4bc854b2087c55ae623d57249
Source dataset
uspto-grants-2008_07
Patent number
US07402600B2

Reaction notes

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