Benzyl Bromide → HCID 11472242, compound

HRID 723007Notes

Reaction equation

HRID 723007 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[N:7]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([OH:11])=[O:10].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O.C(O)C.CN(C=O)C>[N:7]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([O:11][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:10]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 11472242HCID 11472242, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

The solution of 33 mg (0.10 mmol) of Cs2CO3 in 0.1 ml of distilled water was added to the solution of 43 mg (0.20 mmol) Boc-Pro-OH in 2 ml of anhydrous ethanol. The mixture was stirred at room temperature for 40 min and then evaporated to dryness. The residue was dried over anhydrous CaCl2 to provide a colorless powder which was dissolved in 1 ml of DMF. To the DMF solution 34 mg (0.2 mmol) of benzyl bromide was added slowly. The mixture was stirred at 50° C. for 16 hr and the formed precipitates of CsBr were filteled. The filtrate was evaporated to dry. The residue was dissolved in 20 ml of ethyl acetate and the solution was washed with saturated solution of NaHCO3, NaCl and 5% solution of KHSO4 successively. The organic phase was separated and dried over anhydrous NaSO4. After filtration the filtrate was evaporated at 37° C. to provide 54 mg (88%) of the title compound as a colorless syrupy.

Workup

  1. customevaporated to dryness
  2. dry with materialThe residue was dried over anhydrous CaCl2
  3. customto provide a colorless powder which
  4. stirringThe mixture was stirred at 50° C. for 16 hr
  5. customthe formed precipitates of CsBr
  6. customThe filtrate was evaporated
  7. customto dry
  8. dissolutionThe residue was dissolved in 20 ml of ethyl acetate
  9. washthe solution was washed with saturated solution of NaHCO3, NaCl and 5% solution of KHSO4 successively
  10. customThe organic phase was separated
  11. dry with materialdried over anhydrous NaSO4
  12. filtrationAfter filtration the filtrate
  13. customwas evaporated at 37° C.

Sources & evidence

ORD record
ord-9c564ecdeef84e12b2617c18be966a7f
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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