Hydrochloric Acid → (4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4}-triazol-3-ylsulfanyl]-2-heptyloxybenzylamino}phenyl)acetic acid

HRID 1171435Notes

Reaction equation

HRID 1171435 reaction equation
C([O:3][C:4](=[O:45])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([S:20][C:21]3[N:25]([CH3:26])[C:24]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=4)=[N:23][N:22]=3)=[CH:16][C:15]=2[O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:8][CH:7]=1)C.C(=O)([O-])[O-].[K+].[K+].Cl>CO>[C:33]([C:30]1[CH:31]=[CH:32][C:27]([C:24]2[N:25]([CH3:26])[C:21]([S:20][C:17]3[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:9]4[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:45])=[O:3])=[CH:7][CH:8]=4)=[C:15]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:16]=3)=[N:22][N:23]=2)=[CH:28][CH:29]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11227433Ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-ylsulfanyl]-2-heptyloxybenzyl amino}phenyl)acetate

Product 1

HCID 11157700(4-{4-[5-(4-tert-Butylphenyl)-4-methyl-4H-[1,2,4}-triazol-3-ylsulfanyl]-2-heptyloxybenzylamino}phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl(4-{4-[5-(4-tert-butylphenyl)-4-methyl-4H-[1,2,4]-triazol-3-yl sulfanyl]-2-heptyloxybenzylamino}phenyl)acetate obtained in Example 1 (2.5 g, 4 mmol) of a 2M aqueous potassium carbonate solution (32 ml) in methanol (65 ml) is heated under reflux for 3 hours. The organic phase is acidified at room temperature with a 2N hydrochloric acid solution to pH 5. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 4:6 mixture. After evaporation of the solvents, 1.7 g (70%) of the expected compound are recovered in the form of a yellow amorphous solid.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionThe desired product is extracted by addition of ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customa rotary evaporator
  7. customThe product is purified by chromatography on a silica column
  8. washeluted with a heptane/ethyl acetate 4:6 mixture
  9. customAfter evaporation of the solvents, 1.7 g (70%) of the expected compound
  10. customare recovered in the form of a yellow amorphous solid

Sources & evidence

ORD record
ord-4de9de7f3a6141c29f901c1c9fde4213
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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