Sodium Carbonate → Methyl N-[hydroxy(phenoxy)methylidene]valinate

HRID 2379643Notes

Reaction equation

HRID 2379643 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6].[C:11]1([O:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>O.C(Cl)Cl.CN(C)CCN>[CH3:2][O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH:6][C:18]([O:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:19]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 111190Methyl valinate hydrochloride

Product 1

HCID 60952Methyl N-[hydroxy(phenoxy)methylidene]valinateYield 99.6%

Reagents, catalysts & solvents 3

HCID 66053N,N-DimethylethylenediamineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 g (596 mmol) of L-valine methyl ester hydrochloride and 84.92 g (542 mmol) of phenylchloroformate in 600 mL of water and 600 mL methylene chloride at 0° C. was added 139.0 g of Na2CO3 (1.311 mol) in portions. After addition was complete the cooling bath was removed and the solution was stirred at ambient temperature for one hour. The organic layer was separated, 1.0 mL of N,N-dimethylethylenediamine (11.0 mmol) was added to the organic layer and the solution mixed for three minutes. The organic layer was washed with 100 mL of 1M potassium hydrogen sulfate solution. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford 135.65 g of the title compound as white crystalline solid; mp 59.1° C.

Workup

  1. additionAfter addition
  2. customwas removed
  3. customThe organic layer was separated
  4. additionthe solution mixed for three minutes
  5. washThe organic layer was washed with 100 mL of 1M potassium hydrogen sulfate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f86918b8026e481da7de448e2b59c5fc
Source dataset
uspto-grants-1994_11
Patent number
US05362912

Reaction notes

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