Potassium ethanethioate → HCID 86603215, compound

HRID 853207Notes

Reaction equation

HRID 853207 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([OH:13])[CH2:11]I)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]([O-:17])(=[S:16])[CH3:15].[K+]>CC(C)=O>[C:14]([S:16][CH2:11][CH:10]([OH:13])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:17])[CH3:15]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 86603216HCID 86603216, compound

Product 1

HCID 86603215HCID 86603215, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(tert-butyloxycarbonylamino)-3-iodopropan-2-ol (example 22a) (2 g, 6.64 mmol) and potassium thioacetate (0.948 g, 8.30 mmol) were dissolved in acetone (30 ml) and the medium was refluxed for 16 hours. The solvent was vacuum evaporated and the residue was taken up in diethyl ether, then filtered on Celite®. The filtrate was evaporated. The residue obtained (1.69 g) was purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 98:2) then repurified by flash chromatography (eluent: dichloromethane) to give the desired compound in the form of a yellow oil.

Workup

  1. temperaturethe medium was refluxed for 16 hours
  2. customevaporated
  3. filtrationfiltered on Celite®
  4. customThe filtrate was evaporated
  5. customThe residue obtained (1.69 g)
  6. customwas purified by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 98:2)
  7. customthen repurified by flash chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-202f7825de99448495664e249493566c
Source dataset
uspto-grants-2007_08
Patent number
US07253296B2

Reaction notes

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