Dicyclohexylcarbodiimide → HCID 58556916, compound

HRID 453678Notes

Reaction equation

HRID 453678 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([NH:13][CH:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([OH:17])=[O:16])[CH:10]=[CH:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[N:49]12[CH2:56][CH2:55][CH:52]([CH2:53][CH2:54]1)[C@@H:51](O)[CH2:50]2>C1COCC1>[O:16]=[C:15]([O:17][C@@H:51]1[CH:52]2[CH2:55][CH2:56][N:49]([CH2:54][CH2:53]2)[CH2:50]1)[CH:14]([NH:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58556914HCID 58556914, compound

Product 1

HCID 58556916HCID 58556916, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-(allyloxycarbonyl)phenylamino)-2-phenylacetic acid (I3) (2.69 g, 8.64 mmol) in dry THF (80 ml), were added DCC (3.57 g, 17.3 mmol) and HOBt (2.65 g, 17.3 mmol). After 30 minutes, (R)-quinuclidin-3-ol (3.30 g, 25.9 mmol) was added and reaction was stirred at room temperature for 18 hours. The solvent was removed in vacuo and the crude residue was purified by flash-chromatography (DCM/MeOH=97/3+0.3% NH4OH) to obtain allyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (2.40 g, 66.1% yield).

Workup

  1. customreaction
  2. customThe solvent was removed in vacuo
  3. customthe crude residue was purified by flash-chromatography (DCM/MeOH=97/3+0.3% NH4OH)

Sources & evidence

ORD record
ord-9e6bfdf5fe7443d2a3b9666d832059e0
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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