Dicyclohexylcarbodiimide → HCID 58557008, compound

HRID 469486Notes

Reaction equation

HRID 469486 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:7]([OH:9])=[O:8])[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2.[N:23]12[CH2:30][CH2:29][CH:26]([CH2:27][CH2:28]1)[C@@H:25](O)[CH2:24]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[S:1]1[CH:5]=[C:4]([CH:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:7]([O:9][C@@H:25]2[CH:26]3[CH2:29][CH2:30][N:23]([CH2:28][CH2:27]3)[CH2:24]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 58556984HCID 58556984, compound

Product 1

HCID 58557008HCID 58557008, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(benzo[b]thiophen-3-yl)-2-(3-methoxyphenylamino)acetic acid (I46) (1.02 g, 3.25 mmol), (R)-quinuclidin-3-ol (496 mg, 3.90 mmol), DCC (805 mg, 3.90 mmol), and HOBT (597 mg, 3.90 mmol) in dry THF (30 ml) was stirred at r.t. overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 1M K2CO3 and then with brine. 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 95/5) to obtain (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(3-methoxyphenylamino)acetate (213 mg, 15.5% yield over two steps).

Workup

  1. customTHF was evaporated
  2. washwashed twice with 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 to 95/5)

Sources & evidence

ORD record
ord-240d93eebca94834b5d33630715ed977
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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