Triphenylphosphine → 5(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one

HRID 1167423Notes

Reaction equation

HRID 1167423 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:49]1[CH:53]=[N:52][S:51][N:50]=1>C1COCC1>[S:51]1[N:52]=[CH:53][C:49]([O:15][CH2:16][C@@H:17]2[O:21][C:20](=[O:22])[N:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:18]2)=[N:50]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21356617(R)-5-(Hydroxymethyl)-3-phenyloxazolidin-2-oneHCID 178516825HCID 178516825, compound

Product 1

HCID 699806285(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylazodicarboxylate (4.45 g, 22 mmol) was added dropwise to a stirred solution of 5(R)-hydroxymethyl-3-phenyloxazolidin-2-one (Gregory et al. J. Med, Chem, 32, 1673 (1989); 4.25 g,22 mmol), triphenyl phosphine (5.76 g, 22 mmol) and 3-hydroxy-1,2,5-thiadiazole (Weinstock et al, J.Org. Chem, 32, 2823 (1967)) (2.04 g, 20 mmol) in 30 ml THF, in an ice-bath. After stirring at ambient temperature for two hours and evaporating in vacuo, the resulting oil was purified by chromatography (Merck 9385 silica. Gradient elution from isohexane to ca. 50% EtOAc/isohexane to give a white solid. Further purification by flash chromatography on silica using 1% MeOH/dichloromethane was necessary to remove remaining diisopropylcarboxyhydrazine yielding the title product as a white crystalline solid (4.7 g, 83%). MS: ESP+ (M+H)+=278.

Workup

  1. customevaporating in vacuo
  2. customthe resulting oil was purified by chromatography (Merck 9385 silica
  3. washGradient elution from isohexane to ca. 50% EtOAc/isohexane
  4. customto give a white solid
  5. customFurther purification by flash chromatography on silica using 1% MeOH/dichloromethane
  6. customto remove

Sources & evidence

ORD record
ord-03e18d8758014202bc015c20e387e945
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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