Dicyclohexylcarbodiimide → HCID 68815204, compound

HRID 732572Notes

Reaction equation

HRID 732572 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.O.ON1C2C=CC=CC=2N=N1.[CH:29]1([N:35]=[C:36]=NC2CCCCC2)CCC[CH2:31][CH2:30]1.CNCCC>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:12]=[C:11]([O:13][CH:14]([F:16])[F:15])[CH:10]=[C:6]([C:7]([N:35]([CH3:36])[CH2:29][CH2:30][CH3:31])=[O:9])[CH:5]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 12315N-MethylpropylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 68814459HCID 68814459, compound

Product 1

HCID 68815204HCID 68815204, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution containing crude 5-difluoromethoxy-isophthalic acid monomethyl ester (2.5 g, 10 mmol) in THF (20 mL) at room temperature with 1-hydroxybenzotriazole hydrate (1.62 g, 12 mmol), 1,3-dicyclohexylcarbodiimide (12 mL, 1 N, 12 mmol), and n-methylpropylamine (1.23 mL, 12 mmol). Stir at room temperature overnight, filter through a filtering agent, wash with 1:1 ethyl acetate:hexanes (50 mL). Concentrate the combined filtrates and purify (silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes) to give the title compound as a solid (1.6 g, 53%).

Workup

  1. additionTreat a solution
  2. filtrationfilter through a filtering agent
  3. washwash with 1:1 ethyl acetate
  4. concentrationConcentrate the combined filtrates
  5. custompurify
  6. wash(silica gel chromatography, eluting with 0:100 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-ef01abe2895d46799c38f4e2f276e088
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

Loading…