Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate

HRID 469459Notes

Reaction equation

HRID 469459 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([OH:9])=[O:8])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C@@H:23](O)[CH2:22]2.O.N1(O)C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([O:9][C@@H:23]2[CH:24]3[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]3)[CH2:22]2)=[O:8])[C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 914043-Quinuclidinol, (-)-HCID 27960291-Hydroxybenzotriazole hydrateHCID 585569682-(Benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acid

Product 1

HCID 58556957(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetateYield 44.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzo[b]thiophen-3-yl)-2-(phenylamino)acetic acid (I18) (295 mg, 1.04 mmol), (R)-quinuclidin-3-ol (159 mg, 1.25 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (191 mg, 1.25 mmol), and DCC (258 mg, 1.25 mmol) were dissolved in dry THF and stirred at room temperature for 15 hours. The solvent was evaporated, and the crude product was dissolved in EtOAc and washed with NaHCO3, water and brine. The organic phase was dried with Na2SO4, filtered and evaporated under vacuum. The crude product was purified by flash chromatography (DCM/MeOH=9/1) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (180 mg, 44% yield).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude product was dissolved in EtOAc
  3. washwashed with NaHCO3, water and brine
  4. dry with materialThe organic phase was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe crude product was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-605f00844c9a447aac9227ef276524aa
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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