Hydrochloric Acid → HCID 57541856, compound

HRID 2422316Notes

Reaction equation

HRID 2422316 reaction equation
[CH3:1][CH:2]([CH3:38])[CH2:3][CH2:4][N:5]([CH2:17][C:18]1[CH:37]=[CH:36][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:10]=1.O.Cl>CO.O1CCCC1.[OH-].[Na+]>[CH3:1][CH:2]([CH3:38])[CH2:3][CH2:4][N:5]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][O:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:29]=2)=[CH:36][CH:37]=1)[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:10]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 57541908HCID 57541908, compound

Product 1

HCID 57541856HCID 57541856, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-{4-[(4-{[(3-methylbutyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}propanoate (240 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 (220 mg, yield 90%) 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-40745ea549db42bcb4e1df20ceeaf907
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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