Phosphorus tribromide → (S)-4-Methyl-4-(3,4-diformyloxybenzyl)-2,5-oxazolidinedione

HRID 971592Notes

Reaction equation

HRID 971592 reaction equation
P(Br)(Br)Br.[C:5]([NH:15][C@:16]([CH3:33])([C:30]([OH:32])=[O:31])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]=[O:26])=[C:20]([O:27][CH:28]=[O:29])[CH:19]=1)(OCC1C=CC=CC=1)=[O:6]>C(OCC)C>[CH3:33][C@:16]1([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]=[O:26])=[C:20]([O:27][CH:28]=[O:29])[CH:19]=2)[C:30](=[O:32])[O:31][C:5](=[O:6])[NH:15]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 54440584(S)-N-Carbobenzyloxy-3-(3,4-diformyloxyphenyl)-2-methylalanine

Product 1

HCID 54261823(S)-4-Methyl-4-(3,4-diformyloxybenzyl)-2,5-oxazolidinedioneYield 81.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Phosphorous tribromide (0.81g, 3 mmol) in dry ethylether (5 ml) is added dropwise to a solution of (S)-N-carbobenzyloxy-3-(3,4-diformyloxyphenyl)-2-methylalanine (0.4g, 1 mmol) in dry ethylether (10 ml). After stirring 3 hours at 20°-25° under dry nitrogen, the reaction mixture is diluted with dry petroleum ether (40°-60°) (100 ml) and refrigerated 18 hours. The solvent is decanted from the gum which has separated. The gum is dissolved in methylene chloride (2 ml) and precipitated with ethyl ether as a gum. The product (B) is separated and dried 0.1mm/25° for 3 hours over phosphorous pentoxide to afford 0.24g (80%) of gummy solid.

Workup

  1. customThe solvent is decanted from the gum which
  2. customhas separated
  3. dissolutionThe gum is dissolved in methylene chloride (2 ml)
  4. customprecipitated with ethyl ether as a gum
  5. customThe product (B) is separated
  6. dry with materialdried 0.1mm/25° for 3 hours over phosphorous pentoxide

Sources & evidence

ORD record
ord-492aab7c35c54b8faf8f5d359c15d65e
Source dataset
uspto-grants-1979_07
Patent number
US04160712

Reaction notes

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