Dicyclohexylcarbodiimide → HCID 58557024, compound

HRID 469483Notes

Reaction equation

HRID 469483 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH3:18])[C:7]([OH:9])=[O:8])[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:48]12[CH2:55][CH2:54][CH:51]([CH2:52][CH2:53]1)[C@@H:50](O)[CH2:49]2>C1COCC1>[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH3:18])[C:7]([O:9][C@@H:50]2[CH:51]3[CH2:54][CH2:55][N:48]([CH2:53][CH2:52]3)[CH2:49]2)=[O:8])[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557006HCID 58557006, compound

Product 1

HCID 58557024HCID 58557024, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(benzo[b]thiophen-3-yl)-2-(2-ethylphenylamino)acetic acid (I43) (875 mg, 2.81 mmol), HOBT (430 mg, 2.81 mmol), and DCC (1.16 g, 5.62 mmol) in THF (28 ml) was stirred at r.t. for 30 minutes. Then (R)-quinuclidin-3-ol (715 mg, 5.62 mmol) was added, and the reaction mixture was stirred at r.t. overnight. The solvent was evaporated, and the crude product was partitioned between EtOAc and sat. Na2CO3. The organic phase was dried over sodium sulphate, filtered and evaporated to dryness. The crude was purified by flash chromatography (EtOAc/MeOH=3/1) to collect (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(2-ethylphenylamino)acetate (86 mg, 7.3% yield over two steps)

Workup

  1. stirringthe reaction mixture was stirred at r.t. overnight
  2. customThe solvent was evaporated
  3. customthe crude product was partitioned between EtOAc and sat. Na2CO3
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by flash chromatography (EtOAc/MeOH=3/1)

Sources & evidence

ORD record
ord-42988275eb014484827e6373a71e312c
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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