Ethyl Acetate → HCID 88198444, compound

HRID 1274964Notes

Reaction equation

HRID 1274964 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 88198444HCID 88198444, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
30 °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 30° 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-7e0a22a0944f4a15af789949e48302d8
Source dataset
uspto-grants-2000_12
Patent number
US06159961

Reaction notes

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