tert-Butyl bromoacetate → (4R,5S)-3[(2S)-3t-butoxycarbonyl-2-benzylpropionyl]-4-methyl-5-phenyl-oxazolidine-2-one

HRID 373651Notes

Reaction equation

HRID 373651 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:23])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]>C1COCC1>[C:29]([O:28][C:26]([CH2:25][C@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:14]([N:3]1[C@H:2]([CH3:1])[C@H:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:5][C:4]1=[O:13])=[O:23])=[O:27])([CH3:32])([CH3:31])[CH3:30]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 13461718(4R,5S)-4-methyl-5-phenyl-3-(3-phenyl-propionyl)oxazolidine-2-one

Product 1

HCID 18648881(4R,5S)-3[(2S)-3t-butoxycarbonyl-2-benzylpropionyl]-4-methyl-5-phenyl-oxazolidine-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of the resultant compound from Example 65 (12.9 g, 41.7 mmol) in dry THF (100 ml) under nitrogen was added at -78° C. a solution of sodium hexamethyldisilylamide 45.9 ml (1M in THF). After 30 min, t-butyl bromoacetate (13.6 ml, 83.4 mmol) was added as a solution in THF. The resulting reaction mixture was stirred for 1 h at -78° C., quenched with sat. NH4Cl solution (50 ml) and the entire reaction mixture partitioned between diethyl ether and water. The organic layer was separated and the aqueous layer extracted once with ether. The combined organic solutions were washed with 10% HCl, sat. NaHC3O, brine, dried (Na2SO4). filtered, and concentrated. The resulting yellow oil was submitted to silica gel chromatography (flash): yield 12.4 g (70%).

Workup

  1. customThe resulting reaction mixture
  2. customquenched with sat. NH4Cl solution (50 ml)
  3. customthe entire reaction mixture
  4. custompartitioned between diethyl ether and water
  5. customThe organic layer was separated
  6. extractionthe aqueous layer extracted once with ether
  7. washThe combined organic solutions were washed with 10% HCl, sat. NaHC3O, brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-1d0bf03295e54af18781c991133a920f
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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