Benzoyl chloride → HCID 59119728, compound

HRID 434127Notes

Reaction equation

HRID 434127 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]([C@H:13]1[C:17](=[O:18])[O:16][C:15](=[O:19])[NH:14]1)([CH3:12])[CH3:11]>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[C:1]([N:14]1[C@@H:13]([CH:10]([CH3:12])[CH3:11])[C:17](=[O:18])[O:16][C:15]1=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 98988542,5-Oxazolidinedione, 4-(1-methylethyl)-, (4S)-

Product 1

HCID 59119728HCID 59119728, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Benzoyl chloride (295 mg, 2.1 mmol) was dissolved in ethyl acetate (21 mL), followed by the addition of (S)-4-isopropyl-2,5-oxazolidinedione (L-valine-NCA) (286 mg, 2.0 mmol) under ice cooling. Further, a solution of 4-dimethylaminopyridine (257 mg, 2.1 mmol) in ethyl acetate (11 mL) was added dropwise under ice cooling over 20 minutes. The resulting mixture was allowed to rise as was in temperature from 09. After the mixture was stirred at room temperature for 2 hours, a precipitated salt was filtered off, and the filtrate was concentrated under reduced pressure. The concentration residue was re-dissolved in a mixed solvent consisting of ethyl acetate (5 mL) and hexane (5 mL), and insoluble matter was filtered off. The filtrate was concentrated under reduced pressure to afford the title compound as white crystals (351 mg, 80%).

Workup

  1. filtrationa precipitated salt was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe concentration residue was re-dissolved in a mixed solvent
  4. filtrationwas filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8f9bccd4f52843fe8ba1d80dae2cd3a1
Source dataset
uspto-grants-2003_12
Patent number
US06670447B2

Reaction notes

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