Tetrahydrofuran → HCID 22118572, compound

HRID 619228Notes

Reaction equation

HRID 619228 reaction equation
[NH2:1][C:2]1[S:3][C:4]([F:14])=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10]C)=[O:9])[N:6]=1.B(Cl)(Cl)Cl.O1CCCC1.C(=O)(O)[O-].[Na+]>ClCCl.[Cl-].[Na+].O>[NH2:1][C:2]1[S:3][C:4]([F:14])=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 88198444methyl (2Z)-2-(2-amino-5-fluoro-1,3-thiazol-4-yl)-2-hydroxyiminoacetate

Product 1

HCID 22118572HCID 22118572, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of methyl 2-(2-amino-5-fluorothiazol-4-yl)-2-(Z)-(hydroxyimino)acetate (1 g) in dichloromethane (20 ml) was added dropwise 1M borontrichloride solution in dichloromethane (22.8 ml) under ice-cooling with stirring, and the mixture was stirred for 3 hours at 50° C. to 10° C. The resulting solution was poured into a mixture of tetrahydrofuran (30 ml) and brine (15 ml), and adjusted to pH 3.0 with saturated aqueous sodium bicarbonate. The separated organic phase was dried with magnesium sulfate and evaporated in vacuo. The residue was subjected to a column chromatography on silica gel and eluted with a mixture of ethyl acetate and methanol (2:1). The fractions containing the object compound were combined and evaporated in vacuo to give 2-(2-amino-5-fluorothiazol-4-yl)-2-(Z)-(hydroxyimino)acetic acid (330.26 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hours at 50° C. to 10° C
  3. dry with materialThe separated organic phase was dried with magnesium sulfate
  4. customevaporated in vacuo
  5. washeluted with a mixture of ethyl acetate and methanol (2:1)
  6. additionThe fractions containing the object compound
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-aba858d9d5794ac3ba120288936d3e58
Source dataset
uspto-grants-1999_09
Patent number
US05958914

Reaction notes

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