Propargyl bromide → HCID 86588808, compound

HRID 1583055Notes

Reaction equation

HRID 1583055 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:30]=[CH:29][C:16]([C:17]([NH:19][C@@H:20]3[CH2:24][NH:23][CH2:22][C@@H:21]3[C:25]([O:27][CH3:28])=[O:26])=[O:18])=[CH:15][CH:14]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[CH2:38](Br)[C:39]#[CH:40]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([NH:19][C@@H:20]3[CH2:24][N:23]([CH2:40][C:39]#[CH:38])[CH2:22][C@@H:21]3[C:25]([O:27][CH3:28])=[O:26])=[O:18])=[CH:29][CH:30]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 86588809HCID 86588809, compound2×

Product 1

HCID 86588808HCID 86588808, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The TFA salt (403a) (92 mg, 0.15 mmol) was dissolved in 2 mL of chloroform and the solution was cooled to 0° C. Triethylamine (88 mg, 122 μL, 0.87 mmol) and propargyl bromide (65 mg, 50 μL, 0.44 mmol) were added subsequently. The mixture was stirred until disappearance of compound (403a). The solution was diluted with ethyl acetate and washed with H2O and brine, and dried over MgSO4. After filtration and concentration, the residue was purified on silica gel to provide methyl (3S,4S)-4-({4-[(2-methyl-4-quinolinyl)methyl]benzoyl}amino)-1-(2-propynyl)-3-pyrrolidinecarboxylate (36 mg, 56%). MS (AP+): 442 (M+1).

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-20b53d7c7cef471a8102fe259bdd1dcf
Source dataset
uspto-grants-2004_05
Patent number
US06740649B2

Reaction notes

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