Triphosgene → HCID 178501107, compound

HRID 538069Notes

Reaction equation

HRID 538069 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][NH:24][C:25](=[O:34])[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[NH2:33])[CH2:19][CH2:18]1)=[O:16]>CC#N>[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH2:23][N:24]2[C:25](=[O:34])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:33][C:2]2=[O:4])[CH2:19][CH2:18]1)=[O:16]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 178501128HCID 178501128, compound

Product 1

HCID 178501107HCID 178501107, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Triphosgene (1.3 mmol, 0.39 g) was added portion wise to a solution of trans-4-{[2-(2-amino-phenyl)-acetylamino]-methyl}-cyclohexanecarboxylic acid methyl ester (2.6 mmol, 0.75 g) in dry CH3CN (20 mL) under argon at 0° C. Then the mixture was heated at 80° C. for 1 h with microwave irradiation. The excess of reagent was quenched by careful addition of H2O (2 mL), the solvent was removed under reduced pressure and the crude was purify by flash chromatography on silica (EtOAc-ETP 10:90 to 50:50) to obtain the titled compound (0.24 g, yield 30%).

Workup

  1. customThe excess of reagent was quenched by careful addition of H2O (2 mL)
  2. customthe solvent was removed under reduced pressure
  3. customthe crude was purify by flash chromatography on silica (EtOAc-ETP 10:90 to 50:50)

Sources & evidence

ORD record
ord-a64b4e0d56894f78bda28f77b4ff2981
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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