Hydrochloric Acid → 2-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoic acid

HRID 1031208Notes

Reaction equation

HRID 1031208 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([OH:10])=[O:9])[N:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(=O)(O)[O-].[K+].Cl>CN(C)C(=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:11]/[O:12][C:13]([C:16]([OH:18])=[O:17])([CH3:15])[CH3:14])/[C:8]([O:10][S:20]([CH3:19])(=[O:22])=[O:21])=[O:9])[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 516893Potassium BicarbonateHCID 15077653(Z)-2-((((5-Amino-1,2,4-thiadiazol-3-yl)(carboxy)methylene)amino)oxy)-2-methylpropanoic acid

Product 1

HCID 879472882-[(Z)-[1-(5-amino-1,2,4-thiadiazol-3-yl)-2-methylsulfonyloxy-2-oxoethylidene]amino]oxy-2-methylpropanoic acidYield 31.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetic acid (2.74 g) in N,N-dimethylacetamide (45 ml) were added methanesulfonyl chloride (1.15 g) and potassium bicarbonate (1.20 g) under cooling in an ice bath. The mixture was stirred for 2.5 hours at 5° C. and poured into a cold mixture of water (200 ml), ethyl acetate (200 ml) and 1N hydrochloric acid (6 ml). The mixture was stirred for 5 minutes under cooling in an ice bath. The organic layer was separated, washed with cold water (200ml×2) and with a cold saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated. Toluene was added to the residue. To the mixture was added methylene chloride and the mixture was cooled for 10 minutes in an ice bath. The crystals were collected by filtration, washed with methylene chloride and air-dried to give methanesulfonyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetate (1.1 g).

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringThe mixture was stirred for 5 minutes
  3. temperatureunder cooling in an ice bath
  4. customThe organic layer was separated
  5. washwashed with cold water (200ml×2) and with a cold saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. additionToluene was added to the residue
  9. additionTo the mixture was added methylene chloride
  10. temperaturethe mixture was cooled for 10 minutes in an ice bath
  11. filtrationThe crystals were collected by filtration
  12. washwashed with methylene chloride
  13. customair-dried

Sources & evidence

ORD record
ord-74b493f0c9b64b68b062d39c82d0f46d
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

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