Potassium Bromide → (4S,5R)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid

HRID 393399Notes

Reaction equation

HRID 393399 reaction equation
[CH2:1]([C@H:8]1[C@H:12]([CH2:13][OH:14])[O:11][C:10](=[O:15])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[OH:17].[Na+].CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+]>O.C(#N)C>[CH2:1]([C@H:8]1[C@H:12]([C:13]([OH:17])=[O:14])[O:11][C:10](=[O:15])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 10965692HCID 10965692, compoundHCID 23665760Sodium Hypochlorite3×

Product 1

HCID 11401767(4S,5R)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acidYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To (4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one obtained in the same manner as in Example 3 (4.68 g) were added acetonitrile (46.8 ml) and water (46.8 ml), and then sodium hydrogencarbonate (4.68 g), TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy (0.0468 g) and potassium bromide (2.69 g) were added. The mixture was stirred and 12% aqueous sodium hypochlorite solution (35.0 g) was added dropwise at room temperature over 30 min. The mixture was stirred at room temperature for 7 hr, and 12% aqueous sodium hypochlorite solution (14.0 g) was further added. The mixture was stirred for 12 hr and 12% aqueous sodium hypochlorite solution (7.0 g) was further added, which was followed by stirring for 3 hr. The reaction was quenched by adding sodium hydrogensulfite (2.84 g). The reaction mixture was analyzed by HPLC to confirm that (4S,5R)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid (4.67 g, yield 93%) was obtained. The mixture was extracted twice with dichloromethane (50 ml, 50 ml) and the solvent of the organic layer was removed under reduced pressure. The obtained oil was analyzed by HPLC to confirm that (4S,5R)-4-benzyl-2-oxo-5-oxazolidinecarboxylic acid (4.00 g, yield 80%) was obtained.

Workup

  1. stirringThe mixture was stirred at room temperature for 7 hr
  2. stirringThe mixture was stirred for 12 hr
  3. stirringby stirring for 3 hr
  4. customThe reaction was quenched
  5. additionby adding sodium hydrogensulfite (2.84 g)

Sources & evidence

ORD record
ord-fe6e339e722e4ba694acf76efdd038f4
Source dataset
uspto-grants-2004_10
Patent number
US06806384B2

Reaction notes

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