Methanol → HCID 71468391, compound

HRID 2281063Notes

Reaction equation

HRID 2281063 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:30]=[CH:29][C:19]([CH2:20][N:21]5[CH2:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]5=[O:28])=[CH:18][CH:17]=4)=[C:13]([CH:14]=C)[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.C[OH:32]>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:17]=[CH:18][C:19]([CH2:20][N:21]5[CH2:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]5=[O:28])=[CH:29][CH:30]=4)=[C:13]([CH:14]=[O:32])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 86711984HCID 86711984, compound

Product 1

HCID 71468391HCID 71468391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{4-[1-(cyclopropylmethyl)-4-ethenyl-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione [(Example 19, Step 1), 328 mg, 0.817 mmol] in methanol (8.2 mL) and dichloromethane (24.5 mL) was cooled to −78° C. Ozone was bubbled through the mixture until saturated and then removed. Oxygen was bubbled through the solution for 15 minutes and then treated with polymer-bound triphenylphosphine (0.27 g, 3 mmol/g). The mixture was warmed to ambient temperature and stirred for 14 hours. The mixture was filtered and the solid was washed with methanol. The filtrate was concentrated in vacuo and purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound: 1H NMR (400 MHz, CDCl3) 10.39 (s, 1H), 7.86 (d, 1H, J=8.4 Hz), 7.55 (d, 1H, J=8.8 Hz), 7.45 (d, 2H, J=8.2 Hz), 7.39 (d, 2H, J=8.2 Hz), 4.67 (s, 2H), 4.62 (d, 2H, J=6.8 Hz), 3.83 (s, 2H), 3.09 (s, 3H), 1.40-1.46 (m, 1H), 0.67-0.72 (m, 2H), 0.51-0.55 (m, 2H) ppm. LRMS m/z (M+H) 404.2 found, 404.2 required.

Workup

  1. customOzone was bubbled through the mixture until saturated and
  2. customthen removed
  3. customOxygen was bubbled through the solution for 15 minutes
  4. additiontreated with polymer-bound triphenylphosphine (0.27 g, 3 mmol/g)
  5. filtrationThe mixture was filtered
  6. washthe solid was washed with methanol
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified via silica gel chromatography (ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-0c9cc10a5d64450698aa35244538a627
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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