Dicyclohexylcarbodiimide → HCID 67607323, compound

HRID 1619530Notes

Reaction equation

HRID 1619530 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=NC1CCCCC1)=NC1CCCCC1.N1(O)C2C=CC=CC=2N=N1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:10]([O:12][C@@H:47]1[CH:48]2[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]2)[CH2:46]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 21901296[(tert-Butoxycarbonyl)amino](4-fluorophenyl)acetic acid

Product 1

HCID 67607323HCID 67607323, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-(4-fluorophenyl)acetic acid (I49) (725 mg, 2.69 mmol) in THF (20 ml), were added N,N′-methanediylidenedicyclohexanamine (667 mg, 3.23 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (437 mg, 3.23 mmol), and (R)-quinuclidin-3-ol (411 mg, 3.23 mmol). The reaction was stirred at RT for 15 hours, and the solvent was evaporated. The residue was taken up with DCM, the insoluble solid was filtered off, and the organic solution was washed twice with aq. Na2CO3 and then brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5 to 93/7) to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(4-fluorophenyl)acetate (410 mg; 40% yield).

Workup

  1. customthe solvent was evaporated
  2. filtrationthe insoluble solid was filtered off
  3. washthe organic solution was washed twice with aq. Na2CO3
  4. dry with materialbrine, dried over Na2SO4
  5. customevaporated
  6. customThe crude was purified by flash chromatography (DCM/MeOH=95/5 to 93/7)

Sources & evidence

ORD record
ord-5eecaa5fdf2f4d229ba3dc6b94fa8087
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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