tert-Butyl bromoacetate → HCID 86594120, compound

HRID 2212453Notes

Reaction equation

HRID 2212453 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]([CH3:23])([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([OH:22])[CH:16]=1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])O.[Cs+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>CN(C)C=O>[OH:22][C:17]1[CH:16]=[C:15]([CH2:14][C@@:10]([NH:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH3:23])[C:11]([O:13][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[O:12])[CH:20]=[CH:19][C:18]=1[OH:21]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 2734983Cesium bicarbonateHCID 21964610HCID 21964610, compound

Product 1

HCID 86594120HCID 86594120, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 102 (650 mg, 2 mmol) in anhydrous N,N-dimethylformamide (7 mL) in a 50 mL capacity screwcap-septum vial was added cesium hydrogencarbonate (480 mg, 2.5 mmol). After having stirred at room temperature for 30 min, a solution of tert-butyl α-bromoacetate (2.5 mmol) was introduced into the reaction mixture. The resulting mixture was stirred at room temperature for 3 h and then, at 45° C. overnight (˜12 h). The reaction mixture was cooled to room temperature and filtered. The residue was washed with ethyl acetate (25 mL×4). The combined filtrates were washed with water (25 mL×2), dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed over silica gel using a gradient of 10–100% ethyl acetate and hexane to afford 710 mg (81%) of the title compound as a light yellow thick liquid. MS (ESI) m/z 463.16 (M+Na+) and 439.02 (M−H−).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 3 h
  2. customat 45° C.
  3. customovernight (˜12 h)
  4. temperatureThe reaction mixture was cooled to room temperature
  5. filtrationfiltered
  6. washThe residue was washed with ethyl acetate (25 mL×4)
  7. washThe combined filtrates were washed with water (25 mL×2)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was chromatographed over silica gel using a gradient of 10–100% ethyl acetate and hexane

Sources & evidence

ORD record
ord-6c53bf953bc049d2ab5c437c9412f7fa
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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