Dicyclohexylcarbodiimide → HCID 58557033, compound

HRID 469512Notes

Reaction equation

HRID 469512 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][CH:12]([C:16]1[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)[C:13]([OH:15])=[O:14])=[O:4].[N:24]12[CH2:31][CH2:30][CH:27]([CH2:28][CH2:29]1)[C@@H:26](O)[CH2:25]2.O.N1(O)C2C=CC=CC=2N=N1.C(=NC1CCCCC1)=NC1CCCCC1>C1COCC1>[CH3:23][O:22][C:19]1[N:18]=[CH:17][C:16]([CH:12]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[C:13](=[O:15])[O:14][C@@H:26]2[CH:27]3[CH2:30][CH2:31][N:24]([CH2:29][CH2:28]3)[CH2:25]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 914043-Quinuclidinol, (-)-HCID 27960291-Hydroxybenzotriazole hydrateHCID 58557011HCID 58557011, compound

Product 1

HCID 58557033HCID 58557033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-(methoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (I79) (118 mg, 0.37 mmol), (R)-quinuclidin-3-ol (52.2 mg, 0.41 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (62.8 mg, 0.41 mmol), and N,N′-methanediylidenedicyclohexanamine (85 mg, 0.41 mmol) was dissolved in dry THF (10 ml) and stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the crude product was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness to obtain the title compound, which was used in the next step without any further purification.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed twice with 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-6cec409afe39423fa1276a14645cfcdf
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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