Ethanol → HCID 86618340, compound

HRID 1713053Notes

Reaction equation

HRID 1713053 reaction equation
II.[CH2:3]([O:5][C:6](=[O:20])[CH2:7][CH2:8][CH2:9][N:10]1[C:14]([NH2:15])=[C:13]([C:16](=[S:18])[NH2:17])[S:12][C:11]1=[S:19])[CH3:4].[O-]S([O-])(=S)=O.[Na+].[Na+].[CH2:28](O)[CH3:29]>>[CH2:3]([O:5][C:6](=[O:20])[CH:7]([CH2:28][CH3:29])[CH2:8][CH2:9][N:10]1[C:14]2=[N:15][S:18][C:16]([NH2:17])=[C:13]2[S:12][C:11]1=[S:19])[CH3:4]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 807IodineHCID 24477Sodium ThiosulfateHCID 59463470HCID 59463470, compound

Product 1

HCID 86618340HCID 86618340, compoundYield 95%

Procedure

An excess of iodine (I2) in ethanol was added dropwise to a stirred solution of 4-(4-amino-5-thiocarbamoyl-2-thioxo-thiazol-3-yl)-butyric acid ethyl ester (360 mg, 1.18 mmol) in ethanol (25 ml), at 25° C., while monitoring the reaction progress by TLC. Once the reaction was completed, (upon stirring overnight at 25° C.), a solution of Na2S2O3 was added, so as to remove excess of I2, and the resulting solution was neutralized with a 5% solution of NaHCO3. A mixture of water and ethyl acetate was added thereafter, phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and the solvents were evaporated under reduced pressure to give yellow oil. Precipitation in acetonitrile gave 342 mg of Compound 43 (95% yield).

Workup

  1. additionwas added
  2. customso as to remove excess of I2
  3. additionA mixture of water and ethyl acetate
  4. additionwas added
  5. customphases were separated
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. customthe solvents were evaporated under reduced pressure
  10. customto give yellow oil
  11. customPrecipitation in acetonitrile

Sources & evidence

ORD record
ord-f2578662c0d249b3be5f75d438209266
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

Loading…