Acetic Acid → Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

HRID 1975740Notes

Reaction equation

HRID 1975740 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].C(O)(=O)C.C([O-])(=O)C.[Na+].[Cl:26][C:27]1[CH:49]=[CH:48][C:30]([CH2:31][N:32]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)=[CH:36][CH:35]=2)N)=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC.O>[Cl:26][C:27]1[CH:49]=[CH:48][C:30]([CH2:31][N:32]2[C:34]3[C:39](=[CH:38][C:37]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:36][CH:35]=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:29][CH:28]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoateHCID 190983301-(4-Chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine

Product 1

HCID 19098332Methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate (33.2 g; 135 mmol), prepared as in Example 1, step 4, in 300 mL toluene and 150 mL acetic acid was added sodium acetate (12.7 g; 155 mmol) followed by 1-(4-chlorobenzyl)-1-[4-(pyrid-2-ylmethoxy)phenyl] hydrazine (48.4 g; 143 mmol), prepared as in step 4. The reaction mixture was stirred in the dark for 5 days, then was poured into water and extracted with ethyl acetate. Solid sodium bicarbonate was added to the extracts and then filtered. The filtrate was washed with water, dried over magnesium sulfate, and the solvent was evaporated. The product was isolated by flash chromatography (40% diethyl ether in hexane) and then recystallized from ethyl acetate/hexane to yield methyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate.

Workup

  1. extractionextracted with ethyl acetate
  2. additionSolid sodium bicarbonate was added to the extracts
  3. filtrationfiltered
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe product was isolated by flash chromatography (40% diethyl ether in hexane)

Sources & evidence

ORD record
ord-a48a416db2384b2880eeafea8ce50e51
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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