Water → 3-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

HRID 1590709Notes

Reaction equation

HRID 1590709 reaction equation
[C:1]([S:5][CH2:6][C:7](=O)[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].CC([O-])=O.[Na+].Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)N)=[CH:27][CH:26]=1.O>C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:13][O:12][C:10](=[O:11])[C:9]([CH3:15])([CH3:14])[CH2:8][C:7]1[N:31]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[C:28]2[C:27]([C:6]=1[S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=2

Participants

7

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoateHCID 189475691-(4-Chlorobenzyl)-1-(4-methoxyphenyl)hydrazine hydrochloride

Product 1

HCID 117625003-[1-(4-Chlorobenzyl)-3-(t-butylthio)-5-methoxyindol-2-yl]-2,2-dimethylpropanoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

To a solution of 39 g of methyl 5-(t-butylthio)-2,2-dimethyl-4-oxopentanoate in a mixture of 300 mL of toluene and 150 mL of glacial acetic acid was added 15 g of NaOAc and 50 g of 1-(4-methoxyphenyl)-1-(p-chlorobenzyl)hydrazine hydrochloride. The reaction was maintained with stirring at room temperature for 3 days under argon in the dark. The mixture was poured into 3 L of H2O and extracted with 3×500 mL of EtOAc. The ethyl acetate was washed with 3×500 mL of water then solid NaHCO3 was added. The mixture was filtered and the filtrate washed twice with water. The organic phase was dried over MgSO4 and evaporated to dryness to provide the title compound. m.p. 102°-103° C.

Workup

  1. temperatureThe reaction was maintained
  2. extractionextracted with 3×500 mL of EtOAc
  3. washThe ethyl acetate was washed with 3×500 mL of water
  4. additionsolid NaHCO3 was added
  5. filtrationThe mixture was filtered
  6. washthe filtrate washed twice with water
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-fe82e1346b074a8f9601d9a6ef8ea7be
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

Loading…