Dicyclohexylcarbodiimide → HCID 67606948, compound

HRID 1619526Notes

Reaction equation

HRID 1619526 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[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:46]12[CH2:53][CH2:52][CH:49]([CH2:50][CH2:51]1)[C@@H:48](O)[CH2:47]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:10]([O:12][C@@H:48]1[CH:49]2[CH2:52][CH2:53][N:46]([CH2:51][CH2:50]2)[CH2:47]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 16244022[(tert-Butoxycarbonyl)amino](4-methoxyphenyl)acetic acid

Product 1

HCID 67606948HCID 67606948, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-(4-methoxyphenyl)acetic acid (I43) (1.39 g, 4.94 mmol) in dry THF (60 ml), were added N,N′-methanediylidenedicyclohexanamine (1.22 g, 5.94 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (802 mg, 5.94 mmol), and (R)-quinuclidin-3-ol (755 mg, 5.94 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-methoxyphenyl)acetate (630 mg; 33% 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-3bc0da75dff54ae08444a992ef7bc8fd
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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