Hydrochloric Acid → 3-{4-[(4-{[(4-Isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoic acid

HRID 2422318Notes

Reaction equation

HRID 2422318 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([N:9]([CH2:15][C:16]2[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[S:7][CH:8]=1)([CH3:3])[CH3:2].O.Cl>CO.O1CCCC1.[OH-].[Na+]>[CH:1]([C:4]1[N:5]=[C:6]([N:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:26][CH:27]=3)=[CH:34][CH:35]=2)[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[S:7][CH:8]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 57541858Methyl 3-{4-[(4-{[(4-isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoate

Product 1

HCID 575419723-{4-[(4-{[(4-Isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoic acidYield 88.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-{4-[(4-{[(4-isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoate (140 mg) was dissolved in a mixed solvent of methanol (2 mL) and tetrahydrofuran (2 mL), and 2N aqueous sodium hydroxide solution (2 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, acidified with 1N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The ethyl acetate layer was dried using Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated to give the title compound (120 mg, yield 88%) as a pale-yellow oil.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f348630301544a0b8549e069dd629342
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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