Dicyclohexylcarbodiimide → HCID 67607092, compound

HRID 1619524Notes

Reaction equation

HRID 1619524 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[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]([CH3:19])=[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])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 23529223tert-Butoxycarbonylamino-p-tolyl-acetic acid

Product 1

HCID 67607092HCID 67607092, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-p-tolylacetic acid (I40) (1.29 g, 4.86 mmol) in THF (70 ml), are added N,N′-methanediylidenedicyclohexanamine (1.20 g, 5.83 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (0.79 g, 5.83 mmol), and (R)-quinuclidin-3-ol (0.74 g, 5.83 mmol). The reaction was stirred at RT for 15 hours, and then 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 dryness. The crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 7/3) to obtain (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-p-tolylacetate (1.03 g; 57% yield).

Workup

  1. customsolvent 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 to dryness
  6. customThe crude was purified by flash chromatography (EtOAc/MeOH=8/2 to 7/3)

Sources & evidence

ORD record
ord-9f42970732d04c4081fb3fb431e34a3f
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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