Hydrogen Peroxide → HCID 58020285, compound

HRID 1632044Notes

Reaction equation

HRID 1632044 reaction equation
[OH:1]O.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([S:18][C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=3)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1>C(O)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[C:12]([S:18]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=3)=[O:1])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 58020012HCID 58020012, compound

Product 1

HCID 58020285HCID 58020285, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 10% v/v 30% aqueous hydrogen peroxide (w/w) (1 mL) in glacial acetic acid (9 mL) was made. To a slurry of the above compound (P-448) (41.3 mg, 0.100 mmol) in acetic acid (300 uL) was added the hydrogen peroxide solution (96.7 uL, 0.100 mmol hydrogen peroxide). The solution was stirred for 1 hour at room temperature. The solvent was removed under vacuum, and the residue purified by silica gel thin layer chromatography (eluting with 10% acetone in dichloromethane), triturated with diethyl ether (5 mL), filtered, and dried to give the product (P-449) (29.3 mg, 68% yield) as a brown gum. 1H NMR (400 MHz, DMSO-d6) 7.55-7.44 (m, 5H), 7.36-7.32 (m, 5H), 7.20 (s, 1H), 7.04 (d, J=8.4 Hz, 1H), 5.27 (m, 1H), 3.84 (s, 3H), 3.29-3.22 (m, 2H), 1.12 (t, J=7.4 Hz, 1H) ppm. LCMS=97.6% purity. MS (APCI+)=429.1 (M+1).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue purified by silica gel thin layer chromatography (eluting with 10% acetone in dichloromethane)
  3. customtriturated with diethyl ether (5 mL)
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-d672651d22ee4bdabc15ecf72793aa8a
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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