Lithium hydroxide, monohydrate → 2-[4-Chloro-2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenoxy]acetic acid

HRID 482003Notes

Reaction equation

HRID 482003 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C.O.[OH-].[Li+]>CO.C1COCC1.O>[C:19]([O:18][C:16]([NH:15][CH2:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[O:6][CH2:5][C:4]([OH:23])=[O:3])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86753642HCID 86753642, compound

Product 1

HCID 540723652-[4-Chloro-2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The product from Step D was suspended in 1:1:1 methanol/THF/water (9 ml) and lithium hydroxide hydrate (126 mg, 3.0 mmol) was added. After 16 h the volatiles were removed in vacuo and the solution was diluted with water and was washed with ethyl acetate, adding sufficient brine to disperse the emulsion. The aqueous layer was acidified with 5% KHSO4 solution and was extracted with methylene chloride which was then dried (Na2 SO4) and evaporated in vacuo to give the title compound as a solid:

Workup

  1. additionwas added
  2. customAfter 16 h the volatiles were removed in vacuo
  3. additionthe solution was diluted with water
  4. washwas washed with ethyl acetate
  5. additionadding sufficient brine
  6. additionto disperse the emulsion
  7. extractionwas extracted with methylene chloride which
  8. customwas then dried (Na2 SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-bdc57ab3d2f144b6b0736c5c6169abe5
Source dataset
uspto-grants-1998_08
Patent number
US05792779

Reaction notes

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