Lithium Hydroxide → HCID 59363830, compound

HRID 1430624Notes

Reaction equation

HRID 1430624 reaction equation
C([O:3][C:4](=[O:19])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:10]=1)([CH3:7])[CH3:6])C.[OH-].[Li+]>C1COCC1.O>[C:16]([NH:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:19])=[O:3])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59363831HCID 59363831, compound

Product 1

HCID 59363830HCID 59363830, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Acetylamino-phenoxy)-2-methyl-propionic acid ethyl ester (0.6 g, 2.2 mmol) was dissolved in THF (20 ml) and a solution of lithium hydroxide (0.33 g, 7.9 mmol) in water (5.8 ml) was added. The reaction mixture was allowed to stir at RT for 24 h. The solvent was removed under reduced pressure and the aqueous layer was extracted with EtOAc (10 ml). Aqueous layer was basified (pH˜5) with 1 N HCl at 0° C., extracted in EtOAc (2×50 ml) dried over Na2SO4 and concentrated under reduced pressure to afford the acid (0.45 g, 85%). 1H NMR (400 MHz, CDCl3): 1.61 (s, 6H), 2.11 (d, J=6.4 Hz, 3H), 4.65 (brs, 3H), 6.68 (d, J=8.0 Hz, 1H), 7.07 (d, J=8.0 Hz, 1H), 7.17 (t, J=8.0 Hz, 1H), 7.29 (s, 1H), 7.60 (s, 1H); MS (EI) m/z: 238.1 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with EtOAc (10 ml)
  3. customat 0° C.
  4. extractionextracted in EtOAc (2×50 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45c98b779958416888462c99376a22ac
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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