Dichloromethane → HCID 13891073, compound

HRID 1722663Notes

Reaction equation

HRID 1722663 reaction equation
[CH2:1]([C@H:5]1[C@H:9]([CH2:10][CH2:11]OS(C)(=O)=O)[O:8][C:7](=[O:17])[NH:6]1)[CH:2]([CH3:4])[CH3:3].[CH2:18]([SH:26])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H-].[Na+].C(Cl)Cl>C1COCC1.[Cl-].[Na+].O>[CH2:1]([C@H:5]1[C@H:9]([CH2:10][CH2:11][S:26][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:8][C:7](=[O:17])[NH:6]1)[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 781262-PhenylethanethiolHCID 13891069HCID 13891069, compound

Product 1

HCID 13891073HCID 13891073, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a 0° C. solution of 4(S)-isobutyl-5(S)-(2-mesyloxyethyl)-2-oxazolidinone (500 mg, 1.88 mmol) and phenethyl mercaptan (273 mg, 1.98 mmol) in THF (6 mL) was added NaH (95 mg, 1.98 mmol of a 50% dispersion) all at once. The reaction was stirred for 3 hours at room temperature and then distributed between methylene chloride and brine solution. The organic layer was washed with brine solution, dried over MgSO4 and evaporated. The residue was chromatographed on silica gel eluting with 65/35 hexane=ethyl acetate to give 570 mg (98%) of product as an oil.

Workup

  1. washThe organic layer was washed with brine solution
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was chromatographed on silica gel eluting with 65/35 hexane=ethyl acetate

Sources & evidence

ORD record
ord-14b36b7a8e4941f1b99dad23787d8df5
Source dataset
uspto-grants-1989_08
Patent number
US04857507

Reaction notes

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