Ethyl Acetate → methyl (2Z)-2-(2-amino-5-fluoro-1,3-thiazol-4-yl)-2-hydroxyiminoacetate

HRID 619227Notes

Reaction equation

HRID 619227 reaction equation
Cl[CH:2]([F:12])[C:3](=O)[C:4](=[N:9][OH:10])[C:5]([O:7][CH3:8])=[O:6].[NH2:13][C:14]([NH2:16])=[S:15].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CN(C)C(=O)C.O>[NH2:16][C:14]1[S:15][C:2]([F:12])=[C:3](/[C:4](=[N:9]/[OH:10])/[C:5]([O:7][CH3:8])=[O:6])[N:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 178501740HCID 178501740, compound

Product 1

HCID 88198444methyl (2Z)-2-(2-amino-5-fluoro-1,3-thiazol-4-yl)-2-hydroxyiminoacetateYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
300 °C

Procedure

To a solution of methyl 4-chloro-4-fluoro-2-(hydroxyimino)-3-oxobutyrate (7.8 g) in N,N-dimethylacetamide (80 ml) was added thiourea (15 g) under stirring at 300° C. and then the stirring was continued for 12 hours at the same temperature. The resulting solution was powered into a mixture of ethyl acetate (300 ml) and water (400 ml), and adjusted to pH 3.0 with saturated aqueous sodium hydrogencarbonate. The separated organic phase was washed with water (400 ml), and brine (400 ml), and dried with magnesium sulfate and evaporated in vacuo to give methyl 2-(2-amino-5-fluorothiazol-4-yl)-2-(Z)-(hydroxyimino)acetate (2.17 g).

Workup

  1. washThe separated organic phase was washed with water (400 ml), and brine (400 ml)
  2. dry with materialdried with magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-6bde03e72cec44d1babe5a053ee7451a
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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