Triethylamine → HCID 68960296, compound

HRID 1726933Notes

Reaction equation

HRID 1726933 reaction equation
[CH2:1]([N:5]1[C:10](=[O:11])[CH2:9][NH:8][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])=N1)[CH2:2][CH2:3][CH3:4].[CH2:19](N(CC)CC)C.Cl[C:27](Cl)([O:29]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH2:1]([N:5]1[CH:19]=[C:7]2[N:8]([C:27](=[O:29])[O:18][C:13]3[C:12]2=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][C:10]1=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 178448733HCID 178448733, compound

Product 1

HCID 68960296HCID 68960296, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Compound 83 (0.21 g, 0.85 mmol) dissolved in 5 mL dichloromethane, was added triethylamine (0.13 mL, 0.94 mmol). The solution was cooled to 0° C. in an ice bath, and triphosgene (0.28 g, 0.94 mmol) was added. After 15 min, the cooling bath was removed. After the reaction stirred for 45 minutes at room temperature, the reaction was complete by TLC. The reaction was quenched with saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash column chromatography (15-20% ethyl acetate/hexanes), afforded 90 mg (39% yield) of Compound 25 as a yellow oil.

Workup

  1. customthe cooling bath was removed
  2. customThe reaction was quenched with saturated sodium bicarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c48215dda4db46c988a27558ea5a66d9
Source dataset
uspto-grants-2009_02
Patent number
US07494996B2

Reaction notes

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