Pyridine → HCID 10217713, compound

HRID 433812Notes

Reaction equation

HRID 433812 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:20][S:21][CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[C:10]([S:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([OH:18])[C:8](=[O:19])[O:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.[CH3:34][C:35]([CH3:40])([CH3:39])[C:36](Cl)=[O:37]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH2:20][S:21][CH2:22][C:23]2[O:24][CH:25]=[CH:26][CH:27]=2)[C:10]([S:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([O:18][C:36](=[O:37])[C:35]([CH3:40])([CH3:39])[CH3:34])[C:8](=[O:19])[O:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 67299661HCID 67299661, compound

Product 1

HCID 10217713HCID 10217713, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-5-oxo-3-(2-furanylmethylsulfanyl)-2-[(2-furanylmethylsulfanyl)-methyl]-2,5-dihydrofuran-2-carboxylic acid ethyl ester (0.3 g, 0.73 mmol) in methylene chloride (25 mL) were added pyridine (0.19 mL, 2.36 mmol) and trimethylacetyl chloride (0.22 mL, 1.77 mmol, 2.4 eq) under argon atmosphere. The mixture was gently refluxed overnight under argon and then evaporated. The residue was purified by column chromatography eluted with a mixed solvent of hexane and ethyl acetate (4:1, v/v) affording 0.3181 g of 4-(2,2-dimethyl-propionyloxy)-3-(furan-2-ylmethylsulfanyl)-2-(furan-2-ylmethylsulfanylmethyl)-5-oxo-2,5-dihydro-furan-2-carboxylic acid ethyl ester as light yellow oil. 1H NMR (CDCl3, 300.16 MHz) δ (ppm): 7.40-7.37 (m, 2H), 6.35-6.25 (m, 4H), 4.35 (s, 2H), 4.33-4.22 (m, 2H), 3.90 (d, J=14.7 Hz, 1H), 3.80 (d, J=14.7 Hz, 1H), 3.29 (d, J=15.1 Hz, 1H), 2.97 (d, J=15.1 Hz, 1H), 1.37 (s, 9H) and 1.29 (t, J=7.1 Hz, 3H). 13C NMR (CDCl3, 75.48 MHz) δ (ppm): 174.35, 166.32, 163.84, 150.29, 148.27, 144.72, 143.10, 142.64, 136.15, 111.00, 110.47, 109.44, 108.98, 87.64, 63.40, 39.30, 36.15, 29.62, 28.02, 26.99 and 14.04. MS (ESI, rel. int.) m/z: 495 (M+H+, 25), 517 (M+Na+, 100).

Workup

  1. customevaporated
  2. customThe residue was purified by column chromatography
  3. washeluted with a mixed solvent of hexane and ethyl acetate (4:1

Sources & evidence

ORD record
ord-b71d8f9084be4d9383569036806e3364
Source dataset
uspto-grants-2003_12
Patent number
US06667330B2

Reaction notes

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