Acetic Acid → HCID 53627664, compound

HRID 407871Notes

Reaction equation

HRID 407871 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7][C:8]([OH:10])=O)[C:4](=[O:11])[O:3]1.[CH2:13]([SH:15])[CH3:14].C1CCC(N=C=NC2CCCCC2)CC1.C(O)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOCC>[CH3:12][C:2]1([CH3:1])[O:6][C@H:5]([CH2:7][C:8](=[O:10])[S:15][CH2:13][CH3:14])[C:4](=[O:11])[O:3]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6343EthanethiolHCID 10868DicyclohexylcarbodiimideHCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 53627664HCID 53627664, compoundYield 71.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

(R)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid (25 g, 144 mmol) was dissolved in CH2Cl2 (500 mL) and cooled in an ice bath. Ethanethiol (21.2 mL, 287 mmol) and N,N-dimethylpyridin-4-amine (0.351 g, 2.87 mmol) were added followed by DCC (35.5 g, 172 mmol). This mixture was stirred in ice bath for 1 hour, and then 2 hours at ambient temperature. Acetic acid (45 mL) was added and then stirred the mixture for 10 minutes. The reaction mixture was then poured into vigorously stirred ether (400 mL) and filtered. The filtrate was washed with 10% sodium carbonate, water, 0.5 N HCl, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (1-5-10% EtOAc in hexanes) to afford (R)—S-ethyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethanethioate (22.5 g, 103 mmol, 71.8% yield) as a clear colorless oil that solidified to a white solid.

Workup

  1. temperaturecooled in an ice bath
  2. custom2 hours
  3. customat ambient temperature
  4. stirringstirred the mixture for 10 minutes
  5. filtrationfiltered
  6. washThe filtrate was washed with 10% sodium carbonate, water, 0.5 N HCl, water and brine
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified over silica gel (1-5-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f2be078a86ea4a7aaf772ca9c1280ad2
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

Loading…