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

HRID 1590101Notes

Reaction equation

HRID 1590101 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.CC(O)=O>[Cl:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][N:31]2[C:28]3[C:27](=[CH:26][C:25]([O:24][CH3:23])=[CH:30][CH:29]=3)[C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:7]2[CH2:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:35][CH:36]=1

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 methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate in a mixture of 300 mL toluene and 150 mL glacial HOAc acid was added 15 g NaOAc and 50 g 1-(4-methoxyphenyl)-1-(4-chlorobenzyl)hydrazine hydrochloride. The reaction was stirred at room temperature for 3 days under argon in the dark. The mixture was poured onto H2O (1L) and extracted with 3×500 mL EtOAc. The EtOAc was washed with 3×500 mL H2O then once with NaHCO3 solution. The organic phase was dried (MgSO4), evaporated to dryness and the residue crystallised from Et2O/hexane 2:1 to afford the title compound, m.p. 102°-103° C.

Workup

  1. extractionextracted with 3×500 mL EtOAc
  2. washThe EtOAc was washed with 3×500 mL H2O
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated to dryness
  5. customthe residue crystallised from Et2O/hexane 2:1

Sources & evidence

ORD record
ord-74eb3126e43c4f68a4991c94174437ed
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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