Hydrochloric Acid → 3-(5-(Benzyloxy)-2-methylphenyl)-5-(carboxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acid

HRID 1486848Notes

Reaction equation

HRID 1486848 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:29])=[C:13]([C:15]2[CH2:19][C:18]([CH2:24][C:25]([O:27]C)=[O:26])([C:20]([O:22]C)=[O:21])[O:17][N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:29])=[C:13]([C:15]2[CH2:19][C:18]([CH2:24][C:25]([OH:27])=[O:26])([C:20]([OH:22])=[O:21])[O:17][N:16]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118292791Methyl 3-(5-(benzyloxy)-2-methylphenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate

Product 1

HCID 1182927503-(5-(Benzyloxy)-2-methylphenyl)-5-(carboxymethyl)-4,5-dihydro-1,2-oxazole-5-carboxylic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-(5-(benzyloxy)-2-methylphenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazole-5-carboxylate (6.80 g), THF (70 mL), methanol (70 mL), and a 1 M aqueous sodium hydroxide solution (70 mL) was stirred at room temperature for 30 minutes. The reaction mixture was rendered acidic using 6 M hydrochloric acid at 0 C, followed by extraction with ethyl acetate. The extract was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (6.30 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c1ba81a50b5f4226a7627654b6714a25
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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