Dicyclohexylcarbodiimide → HCID 67124909, compound

HRID 469488Notes

Reaction equation

HRID 469488 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=2)[C:7]([OH:9])=[O:8])[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[N:51]12[CH2:58][CH2:57][CH:54]([CH2:55][CH2:56]1)[C@@H:53](O)[CH2:52]2>C1COCC1>[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:7](=[O:9])[O:8][C@@H:53]2[CH:54]3[CH2:57][CH2:58][N:51]([CH2:56][CH2:55]3)[CH2:52]2)[C:3]2[CH:22]=[CH:23][CH:24]=[CH:25][C:2]1=2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124900HCID 67124900, compound

Product 1

HCID 67124909HCID 67124909, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzo[b]thiophen-3-yl)-2-(3-(ethoxycarbonyl)phenylamino)acetic acid (I49) (998 mg, 2.81 mmol), HOBT (430 mg, 2.81 mmol), and DCC (1159 mg, 5.62 mmol) were dissolved in THF (28 ml). The mixture was stirred at r.t. for 30 minutes, and then (R)-quinuclidin-3-ol (714 mg, 5.62 mmol) was added. The resulting 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 sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DCM/MeOH=95/5) to collect ethyl 3-(1-(benzo[b]thiophen-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (222 mg, 17.0% yield over two steps).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at r.t. overnight
  3. customThe solvent was evaporated
  4. customthe crude product was partitioned between EtOAc and sat. Na2CO3
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-bfe2f7654b8248d59fa04600c43123cb
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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