Triethylamine → (4RS,5SR)-4-(4-tert-butoxybenzyl)-5-(3-chlorophenyl)-1,3-oxazolidin-2-one

HRID 1610633Notes

Reaction equation

HRID 1610633 reaction equation
[O:1]([C:6]1[CH:25]=[CH:24][C:9]([CH2:10][CH:11]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[OH:16])C(O)=O)=[CH:8][CH:7]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C([N:45]([CH2:48]C)CC)C>O1CCCC1>[C:2]([O:1][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]2[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)[O:16][C:48](=[O:33])[NH:45]2)=[CH:24][CH:25]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22261916(2RS,3RS)-2-(4-tert-butoxybenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoic acid

Product 1

HCID 22262068(4RS,5SR)-4-(4-tert-butoxybenzyl)-5-(3-chlorophenyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2RS,3RS)-2-(4-tert-butoxylbenzyl)-3-(3-chlorophenyl)-3-hydroxypropanoic acid (4.50 g, 14.3 mmol) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (3.39 ml, 15.7 mmol) and triethylamine (3.00 ml, 21.4 mmol), and the mixture was heated under reflux for 1 hr. The reaction solution was allowed to cool and the mixture was evaporated under reduced pressure. To the residue was added water (200 ml), and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the objective substance (4.01 g, 80%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureto cool
  4. customthe mixture was evaporated under reduced pressure
  5. additionTo the residue was added water (200 ml)
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried (anhydrous magnesium sulfate)
  9. customevaporated under reduced pressure
  10. customThe residue was recrystallized from hexane-ethyl acetate
  11. customto give the objective substance (4.01 g, 80%)

Sources & evidence

ORD record
ord-58aadf9a0b6b42e88a92b32f0459a88d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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