Sodium Hydroxide → HCID 131713639, compound

HRID 358158Notes

Reaction equation

HRID 358158 reaction equation
C1(C([O:14][C:15](=[O:33])[C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][C:20]=2[NH2:32])=[N:17][OH:18])C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+:35]>CO>[Na+:35].[C:25]([C:22]1[CH:23]=[CH:24][C:19]([C:16](=[N:17][OH:18])[C:15]([O-:33])=[O:14])=[C:20]([NH2:32])[CH:21]=1)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131713641HCID 131713641, compound

Product 1

HCID 131713639HCID 131713639, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

50 g of 2-(4-BOC-aminophenyl)-2-hydroxyiminoacetic acid diphenylmethyl ester are boiled under reflux in a mixture of 1660 ml of methanol and 250 ml of 2N aqueous NaOH for 11/2 hours under nitrogen. The reaction mixture is concentrated to 300 ml, diluted with ethyl acetate and washed three times with water. The aqueous washings are combined, cooled to 0° C. and adjusted to a pH of 3 with 2N aqueous hydrochloric acid. Extraction is carried out with ethyl acetate and the organic phase is washed neutral with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated by evaporation in vacuo. 250 ml of water are mixed with the evaporation residue and the pH is adjusted to 7 with 2N aqueous sodium hydroxide solution. The aqueous solution is then extracted with ethyl acetate, the organic phase is washed three times with water, the aqueous washings are combined and filtered through sand, the filtrate is concentrated in vacuo to approximately 50 ml and the product is precipitated by adding 150 ml of ethanol and 500 ml of ether. After filtering off and drying, 2-(4-BOC-aminophenyl)-2-hydroxyiminoacetic acid sodium salt (syn-anti mixture) is obtained.

Workup

  1. concentrationThe reaction mixture is concentrated to 300 ml
  2. additiondiluted with ethyl acetate
  3. washwashed three times with water
  4. extractionExtraction
  5. washthe organic phase is washed neutral with saturated aqueous NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated by evaporation in vacuo
  8. addition250 ml of water are mixed with the evaporation residue
  9. extractionThe aqueous solution is then extracted with ethyl acetate
  10. washthe organic phase is washed three times with water
  11. filtrationfiltered through sand
  12. concentrationthe filtrate is concentrated in vacuo to approximately 50 ml
  13. customthe product is precipitated
  14. additionby adding 150 ml of ethanol and 500 ml of ether
  15. filtrationAfter filtering off
  16. customdrying

Sources & evidence

ORD record
ord-1a7597b158384854918da4ff8602ce0e
Source dataset
uspto-grants-1984_08
Patent number
US04464366

Reaction notes

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