Triethylamine → HCID 86654952, compound

HRID 1615602Notes

Reaction equation

HRID 1615602 reaction equation
[C:1]([O:5][C:6]([C:8]1[N:9]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:10]2[C:15]([C:16]=1[NH2:17])=[CH:14][C:13]([C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:33](Cl)([O:35]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([C:8]1[N:9]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:10]2[C:15]([C:16]=1[N:17]=[C:33]=[O:35])=[CH:14][C:13]([C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 86654951HCID 86654951, compound

Product 1

HCID 86654952HCID 86654952, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 3-amino-1-benzyloxycarbonyl-5-trifluoromethylindole-2-carboxylic acid tert-butyl ester 5D (1.78 g, 4.10 mmol) in anhydrous toluene (40 mL) was added triphosgene (0.42 g, 1.41 mmol) and triethylamine (0.83 g, 8.22 mmol). The reaction mixture was heated under reflux for 2 hours. Toluene (50 mL) was added and the organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure to provide 1-benzyloxycarbonyl-3-isocyanato-5-trifluoromethylindole-2-carboxylic acid tert-butyl ester 5E which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. washthe organic layer was washed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec2215afdfad45a190058511007329d9
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

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