Triethylamine → HCID 11265900, compound

HRID 1774379Notes

Reaction equation

HRID 1774379 reaction equation
[CH2:1]([C@H:8]1[C@H:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](=[O:21])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.BrBr>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.CCCCCC.C(OCC)(=O)C>[CH2:14]([C:13]1[C:12]([O:11][C:9](=[O:10])[C:8]=1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 24408BromineHCID 65367Trimethylsilyl triflateHCID 86619640HCID 86619640, compound

Product 1

HCID 11265900HCID 11265900, compoundYield 25%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To the suspension of (2S,3S)-2,3-dibenzylsuccinic anhydride thus obtained in anhydrous toluene (3.5 mL) were added triethylamine (361 mg, 2.54 mmol) and trimethylsilyltrifluoromethanesulfonic acid (565 mg, 2.54 mmol) with stirring under ice cooling, and the mixture was stirred at 90° C. for 2 h. To the reaction mixture with stirring under ice cooling was added dropwise a solution of tetrabutylammonium bromide (2.7 mg, 0.00845 mmol) in dichloromethane (3 mL) and bromine (140 mg, 0.876 mmol), and the reaction mixture was stirred at the same temperature for 30 min. The reaction mixture was directly concentrated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 8:1) to give 59 mg of the title compound as a solid (2 step yield: 25%).

Workup

  1. stirringthe mixture was stirred at 90° C. for 2 h
  2. stirringTo the reaction mixture with stirring under ice cooling
  3. stirringthe reaction mixture was stirred at the same temperature for 30 min
  4. concentrationThe reaction mixture was directly concentrated under reduced pressure
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-01393d8ff708445fa62ff8611b016139
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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