L-Valine → 2,5-Oxazolidinedione, 4-(1-methylethyl)-, (4S)-

HRID 25852Notes

Reaction equation

HRID 25852 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C@H:6]([C:10]([OH:12])=[O:11])[CH:7]([CH3:9])[CH3:8]>C1(C)C=CC=CC=1.C1COCC1>[CH:7]([C@H:6]1[C:10](=[O:11])[O:12][C:1](=[O:2])[NH:5]1)([CH3:9])[CH3:8]

Participants

5

Reactant 2

HCID 6287L-ValineHCID 6371Phosgene

Product 1

HCID 98988542,5-Oxazolidinedione, 4-(1-methylethyl)-, (4S)-Yield 47.32%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

30.4 ml (57.47 mmol, 1.08 eq.) of a 20% solution of phosgene in toluene were added slowly at r.t. to a stirred solution of 6.26 g (53.44 mmol) L-valine (81a) in 63 ml dry THF. After the complete addition the mixture was heated at 55° C. for 4 h. Then a stream of nitrogen was bubbled through the solution and passed after that through a 1M aq. NaOH-solution for 20 min. before the solvent was evaporated. Recrystallization of the obtained residue from PE/Ether (2:1) yielded 3.62 g (25.29 mmol, 47.32%) (S)-4-Isopropyl-oxazolidine-2,5-dione (86) as a white solid.

Workup

  1. additionAfter the complete addition the mixture
  2. customThen a stream of nitrogen was bubbled through the solution
  3. customfor 20 min.
  4. customwas evaporated
  5. customRecrystallization of the obtained residue from PE/Ether (2:1)

Sources & evidence

ORD record
ord-28457aad1c10465881384379931daa57
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Reaction notes

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