Methyl bromoacetate → HCID 86585710, compound

HRID 1008295Notes

Reaction equation

HRID 1008295 reaction equation
[C:1]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1=[O:20])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>C1COCC1>[CH2:3]([C@@H:2]([C:1]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:11][O:10][C:9]1=[O:20])=[O:7])[CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10612452HCID 10612452, compound

Product 1

HCID 86585710HCID 86585710, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N-hexanoyl-4-(S)-benzyloxazolidin-2-one (7.3 mmol) in THF at −78° C. was added 1.0 M sodium hexamethyldisilazide (NaHMDS, 8.8 mmol) and the reaction stirred at −78° C. for 1 hr. A solution of methyl bromoacetate (8.8 mmol) in THF was then added dropwise, and the resulting mixture was stirred at −78° C. for 1 hr and then at room temperature overnight. The reaction was quenched with NH4Cl, concentrated, then suspended in ethyl acetate and washed with 0.5 N HCl and brine, dried, and purified by silica gel chromatography (ethyl acetate/hexanes) to afford the methyl 3-(R)-(n-butyl)-3-[4-(S)-benzyloxazolidin-2-one-3-ylcarbonyl)propionate.

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 1 hr
  2. customat room temperature
  3. customovernight
  4. customThe reaction was quenched with NH4Cl
  5. concentrationconcentrated
  6. washwashed with 0.5 N HCl and brine
  7. customdried
  8. custompurified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-de2e7c88f09144f2a2fe4d7cddf539f9
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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