Hydrochloric Acid → HCID 69427774, compound

HRID 1295294Notes

Reaction equation

HRID 1295294 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27][C:28]([O-:30])=[O:29])[N:26]=2)=[CH:17][CH:16]=1.O.[OH-].[Li+].O1CCCC1.Cl>CO.O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[S:23][CH:24]=[C:25]([CH2:27][C:28]([OH:30])=[O:29])[N:26]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86591673HCID 86591673, compound

Product 1

HCID 69427774HCID 69427774, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl [2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenylthio]-4-thiazolylacetate (330 mg), lithium hydroxide hydrate (89.0 mg), tetrahydrofuran (3 ml), water (2 ml) and methanol (2 ml) was stirred at room temperature for 4 hrs. 1N Hydrochloric acid (2.2 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give [2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenylthio]-4-thiazolyl]acetic acid (215 mg, yield 69%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 180–181° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e87c58f2a411453ba8df9eb84020428d
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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