HCID 59783807, compound → HCID 59783701, compound

HRID 718127Notes

Reaction equation

HRID 718127 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]1[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=1)=O>CC(O)=O>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]1[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=1

Participants

3

Reactant 1

HCID 59783807HCID 59783807, compound

Product 1

HCID 59783701HCID 59783701, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

AcOH (2 mL) was added to compound 500 (117 mg, 0.329 mmol) and the solution was heated at 90° C. for 30 minutes. The solvent was evaporated under reduced pressure. The residue was then partitioned between ethyl acetate and water and the pH adjusted to pH=10. The organic phase was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with 50-100% EtOAc in hexanes to afford title compound 501 (72 mg, 65%). MS (m/z): 338.4 (M+H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was then partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 50-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-f208305c51c34da9b0ad0ef6217ce0ae
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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