Hydrochloric Acid → (Boc-aminooxy)acetic acid

HRID 1461876Notes

Reaction equation

HRID 1461876 reaction equation
[CH3:1][C:2]([CH3:14])([O:4][C:5]([NH:7][O:8][CH2:9][C:10]([O:12]C)=[O:11])=[O:6])[CH3:3].[OH-].[K+].Cl>CO>[CH3:3][C:2]([CH3:14])([O:4][C:5]([NH:7][O:8][CH2:9][C:10]([OH:12])=[O:11])=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15730207Methyl {[(tert-butoxycarbonyl)amino]oxy}acetate

Product 1

HCID 2755974(Boc-aminooxy)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(1,1-Dimethylethoxy)carbonyl]aminooxyacetic acid, methyl ester (18.0 g, 0.087 mole) and potassium hydroxide (7.4 g, 0.13 mole) were stirred in 60 ml of methanol for one hour at ambient temperatures. The mixture was neutralized with concentrated hydrochloric acid and evaporated to dryness in vacuo. The residue was taken up in 100 ml of water and acidified to pH 2.5. Extraction with ethyl acetate, drying over magnesium sulfate and evaporation gave the title compound as 6.8 g of a colorless solid, m.p. 95°-98° C.

Workup

  1. customevaporated to dryness in vacuo
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying over magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-8bd5b475131346fbac2a98da18320ef7
Source dataset
uspto-grants-1991_12
Patent number
US05077432

Reaction notes

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