Dicyclohexylcarbodiimide → HCID 54763971, compound

HRID 469446Notes

Reaction equation

HRID 469446 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[N:20]12[CH2:27][CH2:26][CH:23]([CH2:24][CH2:25]1)[C@@H:22](O)[CH2:21]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([O:12][C@@H:22]2[CH:23]3[CH2:26][CH2:27][N:20]([CH2:25][CH2:24]3)[CH2:21]2)=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557005HCID 58557005, compound

Product 1

HCID 54763971HCID 54763971, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(6-methoxypyridin-3-yl)-2-(phenylamino)acetic acid (I1) (100 mg, 0.39 mmol), (R)-quinuclidin-3-ol (59.1 mg, 0.46 mmol), HOBT (71.2 mg, 0.46 mmol) and DCC (96 mg, 0.46 mmol) was dissolved in dry THF (10 ml). The resulting reaction was stirred at room temperature overnight. Then solvent was removed under reduced pressure, and the residue was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=98/2) to obtain (R)-quinuclidin-3-yl 2-(6-methoxypyridin-3-yl)-2-(phenylamino)acetate (33 mg, 23% yield).

Workup

  1. customThe resulting reaction
  2. customThen solvent was removed under reduced pressure
  3. washwashed twice with 2M K2CO3
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by flash chromatography (DCM/MeOH=98/2)

Sources & evidence

ORD record
ord-e31d52197c2d4e1793758f05c7afa1a8
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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