HCID 68006700, compound → HCID 67975906, compound

HRID 1053906Notes

Reaction equation

HRID 1053906 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15](=[O:16])[CH2:14][CH2:13][CH:12]2[C:17]2[CH:22]=[CH:21][C:20]([NH:23]C(=O)OC(C)(C)C)=[CH:19][CH:18]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>ClCCl.FC(F)(F)C(O)=O.C(OCC)(=O)C>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([CH:12]2[CH2:13][CH2:14][C:15](=[O:16])[CH:11]2[C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 1

HCID 68006700HCID 68006700, compound

Product 1

HCID 67975906HCID 67975906, compoundYield 59.8%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 7G (1.3 g, 3.19 mmol) in dichloromethane (12 mL) and trifluoroacetic acid (4 mL) was stirred at ambient temperature for 1 hour. The mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 solution (30 mL×3) and brine (30 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (petroleum ether/ethyl acetate=2:1, v/v) to afford the title compound (586 mg, 1.906 mmol, 59.8% yield) as a solid. LC/MS (ESI) m/z 308 (M+H)+.

Workup

  1. washwashed with saturated NaHCO3 solution (30 mL×3) and brine (30 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (petroleum ether/ethyl acetate=2:1

Sources & evidence

ORD record
ord-5b5ac12848784519b817d9994a8fdb2b
Source dataset
uspto-grants-2016_07
Patent number
US09394279B2

Reaction notes

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