HCID 86708920, compound → HCID 86708922, compound

HRID 1522075Notes

Reaction equation

HRID 1522075 reaction equation
[O:1]=[S:2]1(=[O:25])[N:9]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[CH2:8][C:5]2([CH2:7][CH2:6]2)[CH2:4][N:3]1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)(=O)C>[CH3:6][C:5]1([CH3:7])[CH2:8][N:9]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([Cl:17])=[CH:12][C:11]=2[Cl:18])[S:2](=[O:25])(=[O:1])[N:3]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:4]1

Participants

3

Reactant 1

HCID 86708920HCID 86708920, compound

Product 1

HCID 86708922HCID 86708922, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 2-(6,6-dioxido-7-(2,4,6-trichlorophenyl)-6-thia-5,7-diazaspiro[2.5]-octane-5-yl)acetate (50 mg, 0.12 mmol) and Pt(IV)O2 (54 mg, 0.24 mmol) were dissolved in acetic acid (10 mL) in a reactor and then air in the reactor was removed by introducing hydrogen gas, followed by shaking for 14 hr under 50 psi. The resultant was washed with ethyl acetate and filtered over celite. To the filtrate, was added water (50 mL) and neutralized using 1 N NaOH, followed by extraction to obtain the organic layer. The resultant was dried over MgSO4, concentrated under reduced pressure, and purified by column chromatography (hexane:ethyl acetate=8:2), giving the compound of interest (46 mg, 77%, light apricot-colored solid). 1H NMR (300 MHz, CDCl3): δ 7.38 (s, 2H), 4.26-4.19 (q, 2H, J=7.1, 7.1, 7.1 Hz), 4.17 (s, 2H), 3.65 (s, 2H), 3.49 (s, 2H), 1.32-1.27 (t, 3H, J=7.1, 7.1 Hz), 1.22 (s, 6H).

Workup

  1. customair in the reactor was removed
  2. additionby introducing hydrogen gas
  3. washThe resultant was washed with ethyl acetate
  4. filtrationfiltered over celite
  5. additionTo the filtrate, was added water (50 mL)
  6. extractionfollowed by extraction
  7. customto obtain the organic layer
  8. dry with materialThe resultant was dried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. custompurified by column chromatography (hexane:ethyl acetate=8:2)
  11. customgiving the compound of interest (46 mg, 77%, light apricot-colored solid)

Sources & evidence

ORD record
ord-3ce1a0db34ca403ca7b9716382c9dd79
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

Loading…