Dicyclohexylcarbodiimide → HCID 58556945, compound

HRID 1044060Notes

Reaction equation

HRID 1044060 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[C@@H:22](O)[CH2:21]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[F:2][C:3]1[CH:4]=[C:5]([NH:9][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([O:13][C@@H:22]2[CH:23]3[CH2:26][CH2:27][N:20]([CH2:25][CH2:24]3)[CH2:21]2)=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124818HCID 67124818, compound

Product 1

HCID 58556945HCID 58556945, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Fluorophenylamino)-2-phenylacetic acid hydrochloride (I40) (1.34 g, 4.74 mmol), (R)-quinuclidin-3-ol (3.01 g, 23.7 mmol), DCC (1.95 g, 9.47 mmol), and HOBt (1.45 g, 9.47 mmol) were dissolved in THF (60 ml). The reaction was stirred at room temperature overnight. The solvent was evaporated, and the crude product was taken up with EtOAc and washed with NaHCO3 and then with brine. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=9/1) to give (R)-quinuclidin-3-yl 2-(3-fluorophenylamino)-2-phenylacetate (1.17 g, 68.9% yield).

Workup

  1. customThe solvent was evaporated
  2. washwashed with NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-2370d149b2aa421b98cf80226c17ea12
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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