Undecanoyl chloride → (+/-)-6-fluoro-8-undecylamido-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

HRID 279879

Reaction equation

HRID 279879 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]2[O:17][CH2:16][CH2:15][C:8]3([S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])[C:6]=2[CH:7]=1.[C:19](Cl)(=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:30])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:5]2[O:17][CH2:16][CH2:15][C:8]3([S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 87287Undecanoyl chlorideHCID 13998518(+/-)-6-Fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

Product 1

HCID 23322839(+/-)-6-fluoro-8-undecylamido-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

161 mg of (±)-6-fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione were dissolved in 3.5 ml of pyridine and esterified with 135 mg of undecanoyl chloride. After stirring at room temperature for 6 hours, the majority of the pyridine was removed in vacuo, the residue was extracted with three portions of ethyl acetate and two portions of 1N hydrochloric acid, the organic phases were washed neutral with water and with saturated sodium chloride solution, dried with sodium sulfate and concentrated. The residue was chromatographed on silica gel with chloroform/methanol (19:1). With Rf =0.27 there were eluted 182 mg of material in the form of a resin which yielded, from methanol, (±)-6-fluoro-8-undecylamido-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione in the form of colorless crystals of melting point 69°-71° C.

Workup

  1. customthe majority of the pyridine was removed in vacuo
  2. extractionthe residue was extracted with three portions of ethyl acetate and two portions of 1N hydrochloric acid
  3. washthe organic phases were washed neutral with water and with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with chloroform/methanol (19:1)
  7. washWith Rf =0.27 there were eluted 182 mg of material in the form of a resin which

Sources & evidence

ORD record
ord-9f5dfd544bf147c58fb93de6892617fa
Source dataset
uspto-grants-1986_05
Patent number
US04587256

Linked notes

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