Dicyclohexylcarbodiimide → HCID 59401120, compound

HRID 77027Notes

Reaction equation

HRID 77027 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]1([NH:23][CH:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[C:25]([OH:27])=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50](O)[CH2:49]2>C1COCC1>[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50]([O:26][C:25](=[O:27])[CH:24]([NH:23][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:36])[F:37])=[CH:30][CH:29]=1)[CH2:49]2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67425422Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid hydrochloride

Product 1

HCID 59401120HCID 59401120, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (907 mg, 1.21 mmol, loading: 1.33 mmol/g) is suspended in dry THF (10 mL). Phenylamino-(4-trifluoromethyl-phenyl)-acetic acid hydrochloride (I104) (200 mg, 0.60 mmol), HOBT (185 mg, 1.21 mmol), and (R)-quinuclidin-3-ol (230 mg, 1.81 mmol) are added and the mixture is shaken at RT overnight. PS-DCC is filtered off, the filtrate is evaporated and the residue is dissolved in EtOAc and washed with NaHCO3, water and brine. The organic layer is dried over Na2SO4, filtered and evaporated to dryness. The resulting crude compound is purified by filtration through a pad of silica-gel using DCM/MeOH=9/1 as the eluent. The title compound is obtained as a colorless oil (110 mg, 45% yield, mixture of diastereoisomers).

Workup

  1. filtrationPS-DCC is filtered off
  2. customthe filtrate is evaporated
  3. dissolutionthe residue is dissolved in EtOAc
  4. washwashed with NaHCO3, water and brine
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. filtrationThe resulting crude compound is purified by filtration through a pad of silica-gel

Sources & evidence

ORD record
ord-cbe8ae05739d4707bde000cc720c650b
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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