Methanol → HCID 178467896, compound

HRID 1954480Notes

Reaction equation

HRID 1954480 reaction equation
[CH3:1][OH:2].C(N([CH2:8][CH3:9])CC)C.C(O)(=[S:12])C.[CH2:14]([C@H:21](COS(C)(=O)=O)[C:22](O)=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH2:31]>>[CH2:14]([C@@H:21]([CH2:22][C:8](=[O:31])[CH3:9])[C:1]([OH:2])=[S:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 5

HCID 887Methanol2×HCID 962WaterHCID 8471TriethylamineHCID 11817759HCID 11817759, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 178467896HCID 178467896, compound

Procedure

To 1.5 ml of methanol, 405 mg of triethylamine were dissolved. Into this solution, 305 ml of thioacetic acid were dropped and stirred for 30 min. at room temperature. To this solution, 2.2 ml of a methanol solution containing 517 mg of (R)-2-benzyl-3-methanesulfonyloxypropionic acid obtained in Example 7 were added and stirred overnight at room temperature. After the reaction was completed, water was added and methanol was removed under reduced pressure. Ethyl acetate was added and washed with a 1N hydrogen chloride and a saturated sodium chloride aqueous solution. After drying with sodium sulfate anhydride the solvent was removed under reduced pressure, followed by purifying the residue with silica gel column chromatography (n-hexane:acetone:acetic acid=70:30:1), thereby obtaining 396 mg of (S)-2-benzyl-3-acetylthiopropionic acid.

Workup

  1. additionwere added
  2. stirringstirred overnight at room temperature
  3. custommethanol was removed under reduced pressure
  4. additionEthyl acetate was added
  5. washwashed with a 1N hydrogen chloride
  6. dry with materialAfter drying with sodium sulfate anhydride the solvent
  7. customwas removed under reduced pressure
  8. customby purifying the residue with silica gel column chromatography (n-hexane:acetone:acetic acid=70:30:1)

Sources & evidence

ORD record
ord-b65e19fcab4748b39e58c3065f335d87
Source dataset
uspto-grants-2000_09
Patent number
US06121477

Reaction notes

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