Sodium Hydroxide → HCID 68283363, compound

HRID 623994Notes

Reaction equation

HRID 623994 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[O:16][CH:15]=[N:14][C:13]=3[C:17]([O:19]C)=[O:18])[CH:9]=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.Cl>[N:1]1([C:6]2[CH:7]=[C:8]([C:12]3[O:16][CH:15]=[N:14][C:13]=3[C:17]([OH:19])=[O:18])[CH:9]=[CH:10][CH:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68283204HCID 68283204, compound

Product 1

HCID 68283363HCID 68283363, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-(3-(pyrrolidin-1-yl)phenyl)oxazole-4-carboxylate (625 mg, 2.3 mmol) in THF (223 mL) was added 1N aq. NaOH-solution (11 mL) and the resulting mixture was stirred at rt overnight. The reaction mixture was poured in 1N aq. HCl-solution and extracted with EtOAc (75 mL). The organic layer was dried (MgSO4), filtered and concentrated to dryness to afford the title compound as a white solid. LC-MS conditions A: tR=0.78 min, [M+H]+=259.00

Workup

  1. extractionextracted with EtOAc (75 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-68af37ac5eed484a9c3b987ca25124b1
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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