HCID 13891073, compound → HCID 13891081, compound

HRID 1722664Notes

Reaction equation

HRID 1722664 reaction equation
[CH2:1]([C@H:5]1[C@H:9]([CH2:10][CH2:11][S:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8]C(=O)[NH:6]1)[CH:2]([CH3:4])[CH3:3].O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>O1CCOCC1.O>[NH2:6][C@@H:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C@@H:9]([OH:8])[CH2:10][CH2:11][S:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 13891073HCID 13891073, compoundHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 13891081HCID 13891081, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4(S)-isobutyl-5(S)-[2-(phenethylmercapto)ethyl]-2-oxazolidinone (0.52 g, 1.69 mmol) and barium hydroxide octahydrate (1.06 g, 3.38 mmol) in dioxane (60 mL) and water (40 mL) was heated at reflux under N2 for 21 hours. The solid barium carbonate was filtered and the filtrate was partially evaporated. The residue was diluted with water and the resulting solution was extracted with ether. The organic extract was washed with brine solution, dried over MgSO4 and evaporated to a residue. Trituration with cold hexane gave 365 mg (77%) of product, m.p. 95°-96° C.

Workup

  1. temperatureat reflux under N2 for 21 hours
  2. filtrationThe solid barium carbonate was filtered
  3. customthe filtrate was partially evaporated
  4. additionThe residue was diluted with water
  5. extractionthe resulting solution was extracted with ether
  6. extractionThe organic extract
  7. washwas washed with brine solution
  8. dry with materialdried over MgSO4
  9. customevaporated to a residue

Sources & evidence

ORD record
ord-601efbda45da428c97533db7bb6e94cd
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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