m-Chloroperbenzoic acid → HCID 57860921, compound

HRID 644191Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40][CH3:41])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[CH:35]=[CH:34][CH:33]=[CH:32][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=O.[OH-:53].[Ca+2].[OH-:55]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:39]=[C:38]([S:40]([CH3:41])(=[O:55])=[O:53])[CH:37]=[CH:36][C:16]=2[C:17]([NH:19][C:20]2[CH:35]=[CH:34][CH:33]=[CH:32][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=2)=[O:23])=[O:18])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

The 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(methylthio)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide (193 mg, 0.32 mmol) was dissolved in chloroform (5 mL). After the solution had been cooled to 0° C., 3-chloroperoxybenzoic acid (mCPBA) (259 mg, 0.87 mmol, 58% purity) was added in portions. After 30 minutes, the reaction was warmed to room temperature and calcium hydroxide (80 mg, 1.1 mmol) was added. After 5 minutes, the reaction was filtered and the filtrate was concentrated in vacuo. The crude material was purified by flash column chromatography (˜20 g silica, 10% EtOAc/CH2Cl2 through 100% EtOAc) to give the desired product (146 mg, 0.23 mmol, 73%) as a white solid.

Workup

temperaturethe reaction was warmed to room temperature
waitAfter 5 minutes
filtrationthe reaction was filtered
concentrationthe filtrate was concentrated in vacuo
customThe crude material was purified by flash column chromatography (˜20 g silica, 10% EtOAc/CH2Cl2 through 100% EtOAc)

Sources & evidence

ORD record: ord-b3bcf986eae74ef385a0d88425e15ac0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700628B2

Reaction notes

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