Hydrochloric Acid → 2-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid

HRID 648835Notes

Reaction equation

HRID 648835 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](=O)[C:7]([OH:9])=[O:8])[N:3]=[CH:2]1.[NH2:11][O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)(O)[O-].[Na+].Cl.[Cl-].[Na+]>CO.O.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:12][N:11]=[C:6]([C:4]1[N:3]=[CH:2][S:1][CH:5]=1)[C:7]([OH:9])=[O:8])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 12919121tert-Butyl (aminooxy)acetateHCID 13187915HCID 13187915, compound

Product 1

HCID 544727372-t-Butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acidYield 66.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(4-thiazolyl)glyoxylic acid (2.3 g) in methanol (23 ml) and t-butyl 2-aminooxyacetate (2.6 g) was stirred for an hour at ambient temperature. The reaction mixture was added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with saturated aqueous solution of sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and the mixture was saturated sodium chloride. The acidic mixture was extracted with ethyl acetate. The extract layer was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetic acid (syn isomer) (2.8 g), mp. 136°-139° C.

Workup

  1. extractionThe acidic mixture was extracted with ethyl acetate
  2. washThe extract layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-217fe107818444d2a981050eb046e194
Source dataset
uspto-grants-1988_04
Patent number
US04736039

Reaction notes

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