Triethylamine → HCID 53241833, compound

HRID 1505415Notes

Reaction equation

HRID 1505415 reaction equation
[CH3:1][C:2]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[CH:10][CH:9]=1)=[O:6])([CH3:4])[NH2:3].C(N(CC)CC)C.Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH3:4][C:2]1([CH3:1])[NH:3][C:31](=[O:33])[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)=[CH:10][CH:9]=2)[C:5]1=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67235810HCID 67235810, compound2×

Product 1

HCID 53241833HCID 53241833, compoundYield 144%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methyl-N1-(4-{[3-(methyloxy)phenyl]oxy}phenyl)alaninamide (Intermediate 72, 1.33 g) and triethylamine (3.70 mL, 26.6 mmol) in dry dichloromethane (80 mL) at 0° C. was added dropwise a solution of triphosgene (600 mg, 2.022 mmol) in dry dichloromethane (20 mL) and the reaction mixture was stirred for 30 minutes at the same temperature. The reaction was quenched with a saturated solution of ammonium chloride (100 mL) and two phases were separated. Aqueous layer was extracted with dichloromethane (100 mL) and the two organic phases were collected, dried over sodium sulphate, filtered and evaporated. The residue was purified by silica gel chromatography (Biotage system, 100 g SNAP cartridge) using as eluent a gradient and cyclohexane/ethyl acetate from 80/20 to 40/60 to afford the title compound as a white solid (950 mg).

Workup

  1. customThe reaction was quenched with a saturated solution of ammonium chloride (100 mL) and two phases
  2. customwere separated
  3. extractionAqueous layer was extracted with dichloromethane (100 mL)
  4. customthe two organic phases were collected
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (Biotage system, 100 g SNAP cartridge)

Sources & evidence

ORD record
ord-a26be8aa1d534bb28e2ca475d14e55d1
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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