Lithium hydroxide, monohydrate → HCID 69426832, compound

HRID 1592852Notes

Reaction equation

HRID 1592852 reaction equation
C[O:2][C:3](=[O:34])[CH:4]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[Cl:33])[N:5]([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[O:15][CH3:16].O.[OH-].[Li+]>C1COCC1.O>[CH3:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([N:5]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[O:15][CH3:16])[CH:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[C:3]([OH:34])=[O:2])=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69427963HCID 69427963, compound

Product 1

HCID 69426832HCID 69426832, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-methoxybenzoyl)-N-(2,4-dimethoxybenzyl)-(2-chlorophenyl)glycine methyl ester (30 g) in THF (350 ml) is added a solution of lithium hydroxide monohydrate (4.2 g) in water (85 ml) and the mixture is refluxed for 2 h before cooling and evaporation of excess THF in vacuo. The aqueous solution is extracted with ether to remove neutral compounds and the aqueous solution adjusted to pH2 with conc. hydrochloric acid. The acidic solution is extracted with dichloromethane (×3), washed with water, dried (MgSO4) and evaporated in vacuo to give the title compound (27.6 g) as a solid foam.

Workup

  1. temperaturethe mixture is refluxed for 2 h
  2. temperaturebefore cooling
  3. customevaporation of excess THF in vacuo
  4. extractionThe aqueous solution is extracted with ether
  5. customto remove neutral compounds
  6. extractionThe acidic solution is extracted with dichloromethane (×3)
  7. washwashed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-23d3a7cd5ed14e2eb67262cb0b67bc52
Source dataset
uspto-grants-2007_11
Patent number
US07294627B2

Reaction notes

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