Dicyclohexylcarbodiimide → HCID 58556983, compound

HRID 469474Notes

Reaction equation

HRID 469474 reaction equation
[S:1]1[C:5]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([OH:9])=[O:8])=[CH:4][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.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[S:1]1[C:5]([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])=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557010HCID 58557010, compound

Product 1

HCID 58556983HCID 58556983, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(benzo[b]thiophen-2-yl)-2-(phenylamino)acetic acid (I30) (796 mg, 2.81 mmol), (R)-quinuclidin-3-ol (429 mg, 3.37 mmol), HOBT (516 mg, 3.37 mmol), and DCC (696 mg, 3.37 mmol) in THF (30 ml) was stirred at r.t. overnight. THF was evaporated, and the crude product was partitioned between EtOAc and 1M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (DCM/MeOH=98/2) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-2-yl)-2-(phenylamino)acetate (361 mg, 32.7% yield).

Workup

  1. customTHF was evaporated
  2. customthe crude product was partitioned between EtOAc and 1M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography (DCM/MeOH=98/2)

Sources & evidence

ORD record
ord-eff9139cf5394ac49a8cb89a892b820d
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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