Methanol → 2,2'-((5-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetic acid

HRID 68321Notes

Reaction equation

HRID 68321 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][N:9]=[C:10]([C:12]2[O:16][C:15]([N:17]([CH2:24][C:25]([O:27]CC)=[O:26])[CH2:18][C:19]([O:21]CC)=[O:20])=[N:14][CH:13]=2)[CH3:11])=[CH:5][CH:4]=1.CO.O.[OH-].[Li+]>C1COCC1>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][N:9]=[C:10]([C:12]2[O:16][C:15]([N:17]([CH2:24][C:25]([OH:27])=[O:26])[CH2:18][C:19]([OH:21])=[O:20])=[N:14][CH:13]=2)[CH3:11])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 86699628Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetate

Product 1

HCID 765282152,2'-((5-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step 3 (295 mg, 0.62 mmoles) in a mixture of THF (6 ml), methanol (2 ml) and water (2 ml), lithium hydroxide (105 mg, 1.25 mmoles) was added and the reaction mixture was stirred at ambient temperature for 4 hours. The solvents were evaporated under reduced pressure. The residue was dissolved in water and acidified with 1N HCl. White solid seperated was filtered and washed with water & dried over P2O5 under vacuum to give 250 mg (82%) of title product as off white solid.

Workup

  1. additionwas added
  2. customThe solvents were evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. customWhite solid seperated
  5. filtrationwas filtered
  6. washwashed with water
  7. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-8117eb18b54444b9ae5ee61fff184666
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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