Hydrochloric Acid → 2-Benzyloxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid

HRID 569367Notes

Reaction equation

HRID 569367 reaction equation
O.NN.Cl.[NH2:5][O:6][CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[CH:18]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=O)[C:27]([OH:29])=[O:28])[N:25]=1)=[O:19].[OH-].[Na+]>CO.O1CCCC1.N1C=CC=CC=1>[CH2:11]([O:10][C:8]([CH2:7][O:6][N:5]=[C:26]([C:24]1[N:25]=[C:21]([NH:20][CH:18]=[O:19])[S:22][CH:23]=1)[C:27]([OH:29])=[O:28])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 11309879Benzyl 2-(aminooxy)acetateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acid

Product 1

HCID 542157752-Benzyloxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydrazine hydrate (8.0 g) in methanol (16 ml) was added to a suspension of benzyl 2-phthalimidoxyacetate (46.0 g) in tetrahydrofuran (150 ml), and the mixture was stirred at ambient temperature for 30 minutes. To the reaction mixture was added 20% hydrochloric acid under ice-cooling, followed by stirring at the same temperature for 10 minutes. The insoluble substance was filtered off to give a solution containing benzyl 2-aminooxyacetate. To this solution were added (2-formamidothiazol-4-yl)glyoxylic acid (24.7 g) and pyridine (24.8 ml), and the mixture was stirred at ambient temperature for 3 hours. The reaction mixture was adjusted to pH 7.5 with 10% aqueous sodium hydroxide and then washed with ethyl acetate. The resultant aqueous solution was acidified to pH 2.0 with 10% hydrochloric acid, followed by extraction with ethyl acetate. The extract was washed with an aqueous sodium chloride and then dried over magnesium sulfate. The solution was evaporated and the residue was pulverized with diisopropyl ether to give 2-benzyloxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (37 g), mp 152° C. (dec.).

Workup

  1. temperaturecooling
  2. stirringby stirring at the same temperature for 10 minutes
  3. filtrationThe insoluble substance was filtered off
  4. customto give a solution
  5. stirringthe mixture was stirred at ambient temperature for 3 hours
  6. washwashed with ethyl acetate
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe extract was washed with an aqueous sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. customThe solution was evaporated

Sources & evidence

ORD record
ord-1e794906a0624b43b1b70ef38771d407
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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