HCID 18947574, compound → HCID 18950574, compound

HRID 1032979Notes

Reaction equation

HRID 1032979 reaction equation
[Cl:1][C:2]1[CH:43]=[CH:42][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]CC4C=CC5C(=CC=CC=5)N=4)=[CH:13][CH:14]=3)[C:9]([C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[CH:4][CH:3]=1>CN(C=O)C.O>[Cl:1][C:2]1[CH:43]=[CH:42][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18947574HCID 18947574, compound

Product 1

HCID 18950574HCID 18950574, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-[1-(4-chlorobenzyl)-3-trimethylacetyl-5-(quinolin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate (EP 419,049, March 27, 1991, Example 8, Step A) (11.5 g) in 150 mL DMF at 100° C. was added CuCl2.2H2O (4.9 g) in 26 mL H2O. After 7 hours, the solution was cooled, poured onto aqueous NH4OAc, and extracted with EtOAc. The organic phase was washed twice with NH4OAc (aq), washed with brine, dried (MgSO4), and evaporated. Purification of the residue by chromatography on silica gel (8% EtOAc in toluene) gave the title compound as a brown gum.

Workup

  1. temperaturethe solution was cooled
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed twice with NH4OAc (aq)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by chromatography on silica gel (8% EtOAc in toluene)

Sources & evidence

ORD record
ord-578a2a08095b4552b3e47c2c6f70fe51
Source dataset
uspto-grants-1994_05
Patent number
US05308850

Reaction notes

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