Hydrochloric Acid → 3-[5-(2-Carboxyethyl)-1,3-oxazol-2-yl]benzoic acid

HRID 14091

Reaction equation

HRID 14091 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16]C)=[O:15])=[N:8][CH:7]=1.O.[OH-].[Li+].Cl>O1CCCC1.CO.O>[C:3]([CH2:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([OH:16])=[O:15])=[N:8][CH:7]=1)([OH:21])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrate2×HCID 21086154Methyl 3-[5-(3-methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoate

Product 1

HCID 210856903-[5-(2-Carboxyethyl)-1,3-oxazol-2-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To methyl 3-[5-(3-methoxy-3-oxopropyl)-1,3-oxazol-2-yl]benzoate (400 mg, 1.3 mmol) in 2:1:1 tetrahydrofuran/methanol/water (8 mL) is added lithium hydroxide monohydrate (112 mg, 2.7 mmol), and the reaction is stirred 2 h at room temperature. More lithium hydroxide monohydrate (225 mg, 5.4 mmol) is added and the reaction is stirred 16 h at room temperature. The reaction is treated with excess concentrated hydrochloric acid resulting in a precipitate. The precipitate is filtered to give the title compound. ESI MS m/z 260.1 [M−H]−.

Workup

  1. stirringthe reaction is stirred 16 h at room temperature
  2. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-51cfdb464c854c71af3003fe78976b34
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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