Dicyclohexylcarbodiimide → HCID 58556953, compound

HRID 77002Notes

Reaction equation

HRID 77002 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]([CH:36]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:37]([OH:39])=[O:38])[CH3:35])=[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>[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48]([O:38][C:37](=[O:39])[CH:36]([N:34]([C:31]1[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=1)[CH3:35])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH2:47]2

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) is suspended in dry THF (13.5 mL). Then HOBT (0.21 g, 1.35 mmol), [(4-fluoro-phenyl)-methyl-amino]-phenyl-acetic acid hydrochloride (I71) (0.20 g, 0.68 mmol) and (R)-quinuclidin-3-ol (0.26 g, 2.03 mmol) are added. The mixture is shaken at RT overnight. PS-DCC is filtered off, washed with EtOAc and THF. The solution is evaporated and the residue is portioned between EtOAc and water. The organic phase is washed with sat. NaHCO3, dried (Na2SO4) and evaporated. The crude is purified by flash chromatography (DCM/MeOH=95/5) to afford the title compound as a colorless oil (209 mg, 84% yield, mixture of diastereoisomers).

Workup

  1. filtrationPS-DCC is filtered off
  2. washwashed with EtOAc and THF
  3. customThe solution is evaporated
  4. washThe organic phase is washed with sat. NaHCO3
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude is purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-6c8ea732153e4d1d917f42becab5d028
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

Loading…