Hydrochloric Acid → HCID 57541845, compound

HRID 2422282Notes

Reaction equation

HRID 2422282 reaction equation
[CH2:1]([N:7]([CH2:19][C:20]1[CH:39]=[CH:38][C:23]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36]C)=[O:35])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.Cl>CO.O1CCCC1.[OH-].[Na+]>[CH2:1]([N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:28][CH:27]=2)=[CH:38][CH:39]=1)[C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 57541885HCID 57541885, compound

Product 1

HCID 57541845HCID 57541845, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-{4-[(4-{[hexyl(4-phenyl-1,3-thiazol-2-yl)amino]methyl}benzyl)oxy]phenyl}propanoate (250 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 the mixture was 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 pale-yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-ef2975504f4c4924af4872a27489a75b
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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