Dicyclohexylcarbodiimide → HCID 58557009, compound

HRID 469509Notes

Reaction equation

HRID 469509 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[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>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]([C:13]2[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[C:10]([O:12][C@@H:23]2[CH:24]3[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]3)[CH2:22]2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557019HCID 58557019, compound

Product 1

HCID 58557009HCID 58557009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(3-fluorophenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (I76) (48 mg, 0.17 mmol), (R)-quinuclidin-3-ol (24.31 mg, 0.19 mmol), HOBT (29.3 mg, 0.19 mmol), and DCC (39.4 mg, 0.19 mmol) was dissolved in THF (10 ml) and stirred at room temperature overnight. The solvent was evaporated, 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
  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-e2baf26355e74105ace8f7da9298cdba
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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