Dicyclohexylcarbodiimide → HCID 67608105, compound

HRID 1619532Notes

Reaction equation

HRID 1619532 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[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][CH:16]=[C:15]([F:19])[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 19904657HCID 19904657, compound

Product 1

HCID 67608105HCID 67608105, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetic acid (I52) (1.10 g, 4.09 mmol) in THF (50 ml), were added N,N′-methanediylidenedicyclohexanamine (1.01 g, 4.90 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (0.66 g, 4.90 mmol), and (R)-quinuclidin-3-ol (0.62 g, 4.90 mmol). The reaction was stirred at RT for 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 to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetate (1.55 g; quantitative 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

Sources & evidence

ORD record
ord-1f731b292c2146df91d1e9222ac71496
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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