Sodium Carbonate → HCID 131717376, compound

HRID 1196527Notes

Reaction equation

HRID 1196527 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[N:25]1([CH2:30][C@@H:31]2[NH:36][C@@H:35]([C:37]([O:39][CH3:40])=[O:38])[CH2:34][CH2:33][CH2:32]2)[CH2:29][CH2:28][CH2:27][CH2:26]1.[C:41](=[O:44])([O-:43])[O-].[Na+].[Na+]>ClCCl>[C:10]([OH:12])(=[O:11])/[CH:9]=[CH:4]\[C:41]([OH:43])=[O:44].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:36]2[C@@H:31]([CH2:30][N:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[CH2:32][CH2:33][CH2:34][C@@H:35]2[C:37]([O:39][CH3:40])=[O:38])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acidHCID 15123271HCID 15123271, compound

Product 1

HCID 131717376HCID 131717376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3,4-dichlorophenylacetic acid (0.325 g) and carbonyldiimidazole (0.26 g) in dry dichloromethane (10 ml) was stirred at ambient temperature for 1 h. A solution of the product of stage (ii) (0.30 g) in dry dichloromethane (10 ml) was added and the mixture was stirred at ambient temperature for 2 days. The reaction mixture was poured into 2M sodium carbonate solution (50 ml) and extracted with dichloromethane (250 ml). The organic extract was washed with 2M sodium carbonate solution (30 ml), dried and evaporated in vacuo. The residue (0.58 g) was purified by flash chromatography eluting with dichloromethane, methanol and ammonia (200:8:1) as eluant to give the free base of the title compound as a gum (0.76 g). The gum was dissolved in ethyl acetate (50 ml) and treated with a solution of maleic acid (60 mg), in ethyl acetate to give a solid which was crystallised from ethyl acetate to give the title compound as a white solid (0.2 g) m.p. 160°-1°.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 days
  2. extractionextracted with dichloromethane (250 ml)
  3. extractionThe organic extract
  4. washwas washed with 2M sodium carbonate solution (30 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue (0.58 g) was purified by flash chromatography
  8. washeluting with dichloromethane, methanol and ammonia (200:8:1) as eluant

Sources & evidence

ORD record
ord-a3c39037a76d4c6ca43d7341ebee611e
Source dataset
uspto-grants-1992_05
Patent number
US05114945

Reaction notes

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