Triethylamine → HCID 67605946, compound

HRID 1619581Notes

Reaction equation

HRID 1619581 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.[C:54]([O:58][C:59]([NH:61][CH:62]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:63](O)=[O:64])=[O:60])([CH3:57])([CH3:56])[CH3:55]>C1COCC1.C(Cl)Cl>[C:54]([O:58][C:59]([NH:61][CH:62]([C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)[C:63]([NH:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]2)[CH2:9]1)=[O:6])=[O:64])=[O:60])([CH3:57])([CH3:55])[CH3:56]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67605946HCID 67605946, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (500 mg, 1.50 mmol) in THF (15 ml) and DCM (5 ml), was added triethylamine (591 μl, 4.25 mmol), and the reaction was stirred at RT for 10 minutes. Then DCC (309 mg, 1.50 mmol), HOBT (203 mg, 1.50 mmol), and 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (314 mg, 1.25 mmol) were added, and the reaction was stirred at RT for 15 hours. The solvent was evaporated, the residue was taken up with DCM, and the insoluble was removed by filtration. The organic solution was washed twice with 1N Na2CO3 and brine, dried over Na2SO4 and evaporated. The crude was purified by flash chromatography (DCM/MeOH=95/5) to obtain (R)-quinuclidin-3-yl 2-(2-(tert-butoxycarbonylamino)-2-phenylacetamido)-2-phenylacetate (210 mg, 34% yield).

Workup

  1. stirringthe reaction was stirred at RT for 15 hours
  2. customThe solvent was evaporated
  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
  7. customThe crude was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-cc8842ad06044b8facbc9cf52fdc5ff7
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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