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

HRID 327219Notes

Reaction equation

HRID 327219 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-4dbbaffee615465c8d00f849197aa993
Source dataset
uspto-grants-1993_12
Patent number
US05272145

Reaction notes

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