Tetrahydrofuran → HCID 86606824, compound

HRID 1437673Notes

Reaction equation

HRID 1437673 reaction equation
[CH2:1]([C@H:8]1[C@@H:13]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[CH2:12][CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:33][CH2:32][CH2:31]1>C(Cl)(=O)C.CCN(CC)CC>[C:32]([N:10]1[CH2:11][CH2:12][C@H:13]([O:14][CH2:15][C:16]2[CH:17]=[C:18]([C:26]([F:29])([F:27])[F:28])[CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=2)[C@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)(=[O:33])[CH3:31]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 86606823HCID 86606823, compound

Product 1

HCID 86606824HCID 86606824, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6367Acetyl chlorideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of the compound (0.40 g) obtained in Example 404 in THF (4 ml), acetyl chloride (0.075 ml) and Et3N (0.147 ml) were added at room temperature, and the reaction mixture was stirred at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in ethyl acetate. The organic layer was washed with 1 N hydrogen chloride and brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative thin layer chromatography to obtain the title compound as pale yellow oil (0.275 g, 79%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic layer was washed with 1 N hydrogen chloride and brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-b75be65ebd82453b9a2ea0821fb3403c
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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