Lithium hydroxide, monohydrate → HCID 90459944, compound

HRID 588872Notes

Reaction equation

HRID 588872 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:12][CH2:13][C:14]([O:16]CC)=[O:15])=[C:4]([O:19][CH3:20])[CH:3]=1.O[Li].O>C1COCC1.O>[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:12][CH2:13][C:14]([OH:16])=[O:15])=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 90456166Ethyl 2-((4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)amino)acetate

Product 1

HCID 90459944HCID 90459944, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-((4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)amino)acetate (630 mg, 2.12 mmol) in THF (15 mL) and water (5 mL), LiOH.H2O (889 mg, 21.2 mmol) was added and the resulting mixture was stirred at RT for 2 h. The mixture was washed with 20% ethyl acetate/petroleum ether. The aqueous layer was acidified with aqueous HCl (1N) to adjust pH to 3-4 and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford the desired product (200 mg, 33% yield).

Workup

  1. washThe mixture was washed with 20% ethyl acetate/petroleum ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec8e466b768c4a7faf4a43eef4d219bd
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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