Dicyclohexylcarbodiimide → HCID 67608055, compound

HRID 1619584Notes

Reaction equation

HRID 1619584 reaction equation
[C:1]([NH:9][CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[C@@H:19](O)[CH2:18]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[C:1]([NH:9][CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([O:13][C@@H:19]1[CH:20]2[CH2:23][CH2:24][N:17]([CH2:22][CH2:21]2)[CH2:18]1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 2266823-Methyl-2-(phenylformamido)butanoic acid

Product 1

HCID 67608055HCID 67608055, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzamido-3-methylbutanoic acid (780 mg, 3.53 mmol) in THF (25 ml), were added (R)-quinuclidin-3-ol (538 mg, 4.23 mmol), DCC (873 mg, 4.23 mmol) and HOBt (572 mg, 4.23 mmol), and the reaction was stirred at RT for 15 hours. The solvent was evaporated. EtOAc was added, and the insoluble was removed by filtration. The organic solution was washed twice with 1N Na2CO3 and brine, dried over Na2SO4 and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=99/1 to 8/2) to obtain (R)-quinuclidin-3-yl 2-benzamido-3-methylbutanoate (436 mg, 37.4% yield).

Workup

  1. customThe solvent was evaporated
  2. additionEtOAc was added
  3. customthe insoluble was removed by filtration
  4. washThe organic solution was washed twice with 1N Na2CO3 and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe crude was purified by flash chromatography (DCM/MeOH=99/1 to 8/2)

Sources & evidence

ORD record
ord-0a89726c0e254cc2bc5128643d3cd350
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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