Hydrochloric Acid → HCID 86591574, compound

HRID 1294343Notes

Reaction equation

HRID 1294343 reaction equation
[CH3:1][CH:2]([NH:22][C:23]1[S:24][CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:27]=1)[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+].CO.Cl>O.O1CCCC1>[CH3:1][CH:2]([NH:22][C:23]1[S:24][CH:25]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:27]=1)[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86591573HCID 86591573, compound

Product 1

HCID 86591574HCID 86591574, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzyloxy]phenylacetate (510 mg), a 1N aqueous sodium hydroxide solution (2.5 mL), methanol (5 mL) and tetrahydrofuran (10 mL) was stirred at 60° C. for 1 hr. Water was added to the reaction mixture, 1N hydrochloric acid (3 mL) was added to the mixture, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals of 4-[4-[methyl(4-phenyl-2-thiazolyl)aminomethyl]benzyloxy]phenylacetic acid. The crystals were recrystallized from diethyl ether-hexane to give colorless prism crystals (427 mg, 87%). melting point: 116-118° C.

Workup

  1. additionwas added to the mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-255598c3f7144b80bd2ba7da2efc0dd4
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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