Acetic Acid → Ethanethioic acid trans-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

HRID 1290349Notes

Reaction equation

HRID 1290349 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1.ClC(Cl)(Cl)[C:14]([N:16]=C=O)=[O:15].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.O1CCCC1.O>[NH2:16][C:14]([O:1][CH2:2][C@@H:3]1[O:7][CH2:6][C@@H:5]([S:8][C:9](=[O:11])[CH3:10])[CH2:4]1)=[O:15]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 76400Trichloroacetyl isocyanateHCID 2724141Tetrabutylammonium FluorideHCID 15346553Ethanethioic acid trans-(+/-)-S-[tetrahydro-5-(hydroxymethyl)-3-furanyl]ester

Product 1

HCID 86752560Ethanethioic acid trans-(+/-)-S-[5-[[(aminocarbonyl)oxy]methyl]tetrahydro-3-furanyl]ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a -20° C. solution, under argon, of 0.406 g of product from Example 6 in 30 ml of methylene chloride is added 0.3 ml of trichloroacetyl isocyanate. The reaction is followed by thin layer chromatography (tlc). When reaction is complete, 1.16 ml of acetic acid, 0.54 ml of water and 9.84 ml of 1M tetrabutylammonium fluoride in tetrahydrofuran is added. The mixture is stirred at room temperature overnight followed by concentration in vacuo. The residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane) to give 0.430 g of the desired product.

Workup

  1. customWhen reaction
  2. concentrationfollowed by concentration in vacuo
  3. customThe residue is purified by chromatography (Silica Gel: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-257d5a627116482c9d003c536f44e76d
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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