Hydrochloric Acid → 2,2'-(3-(5-(Benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetic acid

HRID 1486865Notes

Reaction equation

HRID 1486865 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Br:30])=[C:13]([C:15]2[CH2:19][C:18]([CH2:25][C:26]([O:28]C)=[O:27])([CH2:20][C:21]([O:23]C)=[O:22])[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>[Cl-].[Na+].O.CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([Br:30])=[C:13]([C:15]2[CH2:19][C:18]([CH2:25][C:26]([OH:28])=[O:27])([CH2:20][C:21]([OH:23])=[O:22])[O:17][N:16]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 118292777Dimethyl 2,2'-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate

Product 1

HCID 1182927882,2'-(3-(5-(Benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetic acidYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of dimethyl 2,2′-(3-(5-(benzyloxy)-2-bromophenyl)-4,5-dihydro-1,2-oxazole-5,5-diyl)diacetate (12.0 g), THF (120 mL), methanol (120 mL), and a 1 M aqueous sodium hydroxide solution (120 mL) was stirred at room temperature for 3 hours. The reaction mixture was rendered acidic using 6 M hydrochloric acid at 0 C, and brine was added thereto, 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 (9.75 g).

Workup

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

Sources & evidence

ORD record
ord-b964c4df10534146b169644a656913d5
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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