Methanol → HCID 20312409, compound

HRID 2420010Notes

Reaction equation

HRID 2420010 reaction equation
C([O:5][C:6](=[O:24])[CH:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[OH:23])[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])CCC.CO.C(=O)(O)[O-].[Na+]>O>[C:12]([O:11][C:9]([NH:8][CH:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[OH:23])[C:6]([OH:24])=[O:5])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 20312442HCID 20312442, compound2×

Product 1

HCID 20312409HCID 20312409, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a boiling solution of 23 g. (0.067 mol.) of N-t-butoxycarbonyl-2-(2,4-dihydroxyphenyl)glycine n-butyl ester in 300 ml. of methanol was slowly added a solution of 23 g. of sodium bicarbonate in 300 ml. of water. During addition, the reaction mixture was kept under a nitrogen atmosphere and the methanol was allowed to distill from the mixture. When all the methanol had been distilled the mixture was cooled, adjusted to pH 7.0 with phosphoric acid and extracted with ethyl acetate. The aqueous phase was acidified to pH 4.0 and again extraced with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to give the title compound.

Workup

  1. additionDuring addition
  2. distillationto distill from the mixture
  3. distillationWhen all the methanol had been distilled the mixture
  4. temperaturewas cooled
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c4179ae142d454096fc33c67a05da8f
Source dataset
uspto-grants-1978_08
Patent number
US04108854

Reaction notes

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