tert-Butyl bromoacetate → HCID 69103938, compound

HRID 2250235Notes

Reaction equation

HRID 2250235 reaction equation
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([N:10]2[CH:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][O:12][C:11]2=[O:22])=[O:9])[C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]1=2.C([N-]C(C)C)(C)C.[Li+].Br[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>O1CCCC1>[C:40]([O:39][C:37](=[O:38])[CH2:36][C@H:7]([CH2:6][C:4]1[C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=2[S:1][CH:5]=1)[C:8]([N:10]1[CH:14]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][O:12][C:11]1=[O:22])=[O:9])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 21102160HCID 21102160, compound

Product 1

HCID 69103938HCID 69103938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(3-benzo[b]thiophen-3-yl-propionyl)-4-benzyl-oxazolidin-2-one (3.35 g, 9.18 mmol) in 100 mL anhydrous tetrahydrofuran at −78° C. was added lithium diisopropyl amide in tetrahydrofuran (6.1 mL, 11.01 mmol) and the reaction mixture was stirred for 30 min Following addition of t-butyl bromoacetate (1.62 mL, 11.01 mmol) at −78° C., the mixture was stirred overnight while it was allowed to warm to room temperature. The solvent was evaporated and the residue diluted with ethyl acetate. The organic layer was washed with water (3×100 mL), dried, filtered, and concentrated to give the crude product. The title product was obtained by filtration through a pad of silica, eluting with methylene chloride (49%).

Workup

  1. stirringthe mixture was stirred overnight while it
  2. customThe solvent was evaporated
  3. additionthe residue diluted with ethyl acetate
  4. washThe organic layer was washed with water (3×100 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product

Sources & evidence

ORD record
ord-f0700549394a4030b94c06843a52004c
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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