Dicyclohexylcarbodiimide → HCID 58556953, compound

HRID 1044037Notes

Reaction equation

HRID 1044037 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.Cl.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH3:45])[CH:35]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=1.[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48](O)[CH2:47]2>C1COCC1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH3:45])[CH:35]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:36]([O:38][C@@H:48]2[CH:49]3[CH2:52][CH2:53][N:46]([CH2:51][CH2:50]3)[CH2:47]2)=[O:37])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124664[(4-Fluoro-phenyl)-methyl-amino]-phenyl-acetic acid hydrochloride

Product 1

HCID 58556953HCID 58556953, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (1.02 g, 1.35 mmol, loading: 1.33 mmol/g) was suspended in dry THF (13.5 ml). HOBT (0.21 g, 1.35 mmol), 2-((4-fluorophenyl)(methyl)amino)-2-phenylacetic acid hydrochloride (I6) (0.20 g, 0.68 mmol), and (R)-quinuclidin-3-ol (0.26 g, 2.03 mmol) were added. The mixture was shaken at RT overnight. PS-DCC was removed by filtration, washed with EtOAc and THF. The solution was evaporated, and the residue was partitioned between EtOAc and water. The organic phase was washed with saturated NaHCO3, dried with Na2SO4, and evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5) to afford the title compound (209 mg, 84% yield, mixture of diastereomers).

Workup

  1. customPS-DCC was removed by filtration
  2. washwashed with EtOAc and THF
  3. customThe solution was evaporated
  4. customthe residue was partitioned between EtOAc and water
  5. washThe organic phase was washed with saturated NaHCO3
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customThe crude was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-2568447594d04a50b843b1576513bf89
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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