Water → HCID 13589046, compound

HRID 1195051Notes

Reaction equation

HRID 1195051 reaction equation
P(OCC)(OCC)(OCC)=O.C([O-])(=O)C.[Na+].O.[Na+].[NH2:19][C:20]1[S:21][CH:22]=[C:23](/[C:25](=[N:29]/[O:30][CH2:31][C:32]#[N:33])/[C:26]([O-:28])=[O:27])[N:24]=1>C(OCC)(=O)C.[Pd](Cl)Cl>[NH2:19][C:20]1[S:21][CH:22]=[C:23](/[C:25](=[N:29]/[O:30][CH2:31][C:32]#[N:33])/[C:26]([OH:28])=[O:27])[N:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6535Triethyl PhosphateHCID 517045Sodium AcetateHCID 88629799HCID 88629799, compound

Product 1

HCID 13589046HCID 13589046, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2.66 g (0.01 mol) of allyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetic in 100 ml of ethyl acetate are treated while stirring with 17.73 mg (0.001 mol) of palladium chloride and 0.083 ml (0.0005 mol) of triethyl phosphate. After stirring for 10 minutes, 0.9 g (0.11 mol) of sodium acetate is added thereto. The reaction occurs after the addition of 1 ml of water and crude 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetic acid sodium salt precipitates out. The mixture is stirred at room temperature for a further 24 hours, subsequently extracted twice with 30 ml of water each time, the aqueous solution is extracted once with ether and subsequently adjusted to pH 2 with 2N aqueous hydrochloric acid. After evaporation to dryness, the residue is dissolved in 50 ml of methanol, filtered and cooled. There are obtained 1.1 g (45.4%) of 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetic acid of melting point 140°-142° C. (decomposition).

Workup

  1. customprecipitates out
  2. stirringThe mixture is stirred at room temperature for a further 24 hours
  3. extractionsubsequently extracted twice with 30 ml of water each time
  4. extractionthe aqueous solution is extracted once with ether
  5. customAfter evaporation to dryness
  6. dissolutionthe residue is dissolved in 50 ml of methanol
  7. filtrationfiltered
  8. temperaturecooled

Sources & evidence

ORD record
ord-ca1b28443e204dbf97b43d70742c8a28
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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