HCID 89955232, compound → HCID 86710152, compound

HRID 705341Notes

Reaction equation

HRID 705341 reaction equation
[CH:1]1([C:4]2[C:5]([N:23]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[S:24]([CH3:27])(=[O:26])=[O:25])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([CH:19]=[N:20]O)[C:8]=3[CH:22]=2)[CH2:3][CH2:2]1>C(OC(=O)C)(=O)C>[C:19]([C:9]1[C:8]2[CH:22]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:5]([N:23]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[S:24]([CH3:27])(=[O:26])=[O:25])=[CH:6][C:7]=2[O:11][C:10]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)#[N:20]

Participants

3

Reactant 1

HCID 89955232HCID 89955232, compound

Product 1

HCID 86710152HCID 86710152, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of Example 8A (1.3 g, 2.56 mmol) in acetic anhydride (40 mL) was heated at 140° C. for 16 hours, cooled and concentrated. The residue was dissolved in ethyl acetate, washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was flash chromatographed on an Isco 12 g silica cartridge eluting with hexane followed by 3:2 hexane/ethyl acetate to give the title compound as a white foam (1.23 g, 98%).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on an Isco 12 g silica cartridge
  9. washeluting with hexane

Sources & evidence

ORD record
ord-704dfef7f4624b2e8703a4d86cb9b598
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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