Hydrogen Peroxide → HCID 11524855, compound

HRID 408530Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]([C:17]2([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH2:19][CH2:18]2)=[O:16])=[N:11][CH:10]=1.OO.CC[O:32]CC.O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:9]1[S:13][C:12]([NH:14][C:15]([C:17]2([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:18][CH2:19]2)=[O:16])=[N:11][CH:10]=1)=[O:32]

Participants

Conditions

Temperature: 85 °C

Procedure

1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid [5-(2-chloro-phenylsulfanyl)-thiazol-2-yl]-amide (50.0 mg, 0.120 mmol) was dissolved in 3 mL of acetic acid containing hydrogen peroxide (30% aqueous solution, 40.8 mg, 0.360 mmol). The mixture was warmed to 85° C. for 1 hour. Ether (1.5 mL) and water (1.5 mL) was added and the layers were separated. the organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. The crude reaction mixture was then separated by reverse-phase preparative liquid chromatography to yield the pure product (19.7 mg, 0.0439 mmol, 36.6%). ESI-MS m/z calc. 448.0. found; 449.1 (M+1)+ Retention time 3.53 minutes. 1H NMR (400 MHz, CD3CN) δ 1.23-1.35 (m, 2H), 1.61-1.68 (m, 2H), 3.80 (s, 3H), 6.90-7.00 (m, 2H), 7.34-7.41 (m, 2H), 7.54-7.68 (m, 3H), 8.03-8.10 (m, 1H), 8.22-8.30 (m, 1H), 9.32 (s, 1H).

Workup

customthe layers were separated
dry with materialthe organic layer was dried over sodium sulfate
filtrationfiltered
customevaporated to dryness
customThe crude reaction mixture
customwas then separated by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record: ord-4301237e0320427bbb5e78fde092dd6b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759335B2

Reaction notes

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