Hydrochloric Acid → 2-(2-Formamido-5-chlorothiazol-4-yl)-2-(1-tert-butoxycarbonylethoxyimino)acetic acid

HRID 1903766Notes

Reaction equation

HRID 1903766 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([Cl:16])=[C:7]([C:9](=O)[C:10]([O:12]CC)=[O:11])[N:8]=1)=[O:2].[OH-].[K+].Cl.[C:20]([O:24][C:25]([CH:27]([O:29][NH2:30])[CH3:28])=[O:26])([CH3:23])([CH3:22])[CH3:21].C(=O)(O)[O-].[Na+]>O1CCCC1.N1C=CC=CC=1>[CH:1]([NH:3][C:4]1[S:5][C:6]([Cl:16])=[C:7]([C:9](=[N:30][O:29][CH:27]([C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:26])[CH3:28])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 14326717Ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylateHCID 19978722Tert-butyl 2-(aminooxy)propanoate

Product 1

HCID 537367052-(2-Formamido-5-chlorothiazol-4-yl)-2-(1-tert-butoxycarbonylethoxyimino)acetic acidYield 16.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylate (10.0 g) was added to the 1 N aqueous solution of potassium hydroxide (76.1 ml) at ambient temperature and stirred for 10 minutes. The reaction mixture was adjusted to pH 2.0 with 10% aqueous hydrochloric acid under ice cooling. A solution of 1-tert-butoxycarbonylethoxyamine (8.4 g) in tetrahydrofuran (35 ml) was added to the stirred suspension of the above mixture in pyridine (13.9 ml) at ambient temperature and stirred for 4 hours at same temperature. The resulting mixture was adjusted to pH 7.5 with a saturated aqueous solution of sodium bicarbonate, and washed with ethyl acetate. The separated aqueous layer was adjusted to pH 2.0 with 10% aqueous hydrochloric acid and extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diisopropyl ether and collected by filtration to give 2-(2-formamido-5-chlorothiazol-4-yl)-2-(1-tert-butoxycarbonylethoxyimino)acetic acid (syn isomer) (2.31 g).

Workup

  1. stirringstirred for 4 hours at same temperature
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. washThe residue was washed with diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-eb5a60b76840464dbd2b60491170e1da
Source dataset
uspto-grants-1984_03
Patent number
US04438113

Reaction notes

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