Dicyclohexylcarbodiimide → HCID 46840709, compound

HRID 1044046Notes

Reaction equation

HRID 1044046 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[NH:25][CH:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27]([OH:29])=[O:28].C1C=CC2N(O)N=NC=2C=1.[N:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48](O)[CH2:47]2>C1COCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[NH:25][CH:26]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:27]([O:29][C@@H:48]1[CH:49]2[CH2:52][CH2:53][N:46]([CH2:51][CH2:50]2)[CH2:47]1)=[O:28]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124668HCID 67124668, compound

Product 1

HCID 46840709HCID 46840709, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (914 mg, 1.301 mmol, loading: 1.33 mmol/g) was suspended in dry THF (15 ml). 2-(2,5-Difluorophenylamino)-2-phenylacetic acid hydrochloride (I20) (195 mg, 0.65 mmol), HOBT (199 mg, 1.30 mmol), and (R)-quinuclidin-3-ol (248 mg, 1.95 mmol) were added, and the suspension was shaken at RT for 16 hours (Conversion complete by UPLC-MS). PS-DCC was removed by filtration under suction, and the filtrate was evaporated. The resulting residue was dissolved in EtOAc and washed with sat. NaHCO3, water and brine. The organic layer was separated, dried over Na2SO4, filtered and evaporated. The crude was purified by filtration through a silica-pad using DCM/MeOH=95/5 as the eluent. The title compound is collected (195 mg, 80% yield, mixture of diastereomers).

Workup

  1. customPS-DCC was removed by filtration under suction
  2. customthe filtrate was evaporated
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed with sat. NaHCO3, water and brine
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe crude was purified by filtration through a silica-pad
  10. customThe title compound is collected
  11. addition(195 mg, 80% yield, mixture of diastereomers)

Sources & evidence

ORD record
ord-621cf7bdaa0249fa8397d51b3e010f0c
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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