Methanol → HCID 68282188, compound

HRID 68313Notes

Reaction equation

HRID 68313 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:12]([O:14]CC)=[O:13])=[N:8][CH:9]=1)(=[O:3])[CH3:2].CO.O.[OH-].[Li+]>C1COCC1>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 68282040HCID 68282040, compound

Product 1

HCID 68282188HCID 68282188, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of step 1 (1.1 gm, 5.3 mmoles) in a mixture of THF (12 ml), methanol (4 ml) and water (4 ml), lithium hydroxide (444 mg, 10.6 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, acidified with 1N HCl and evaporated in vacuum. The residue was diluted with ethyl acetate, stirred for 30 min and filtered. The filtrate was concentrated in vacuum to yield 1.0 gm (98%) 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. customevaporated in vacuum
  5. additionThe residue was diluted with ethyl acetate
  6. stirringstirred for 30 min
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-62a31ce45ca14c548857493d305dfc33
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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