HCID 67159662, compound → HCID 67158952, compound

HRID 1255185Notes

Reaction equation

HRID 1255185 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:21])[CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1>C(O)(=O)C.O>[CH3:21][C:13]1[CH:12]=[C:11]([CH:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)[CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 1

HCID 67159662HCID 67159662, compound

Product 1

HCID 67158952HCID 67158952, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of the title compound from Example 13 Step C (610 mg, 2.10 mmol) in acetic acid (7.8 mL) and water (2.6 mL) was stirred at 80° C. After 2 h, the mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. The resulting oil was diluted with ether, then was washed successively with water, saturated aqueous sodium bicarbonate, water, and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes, then 50 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 215.4 [M−CH3O]+; 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=8.5 Hz, 1H), 7.14-7.10°(m, 2H), 3.88 (s, 3H), 3.05-3.00 (m, 1H), 2.59 (s, 3H), 2.51 (app dd, J=8.5, 4.0 Hz, 4H), 2.24-2.20 (m, 2H), 1.97-1.92 (m, 2H).

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe resulting oil was diluted with ether
  3. washwas washed successively with water, saturated aqueous sodium bicarbonate, water, and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-aa13f24b38e04a8f95210ccfb885e6de
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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