Nitrilooxonium tetrafluoroborate → HCID 69388350, compound

HRID 860962Notes

Reaction equation

[F:1][B-](F)(F)F.N#[O+].[CH3:8][N:9]([C:14](=[O:36])[C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([O:22][C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[C:26]([O:32][CH3:33])=[C:25](N)[CH:24]=2)=[C:17]([Cl:35])[CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12]>ClCCl>[CH3:8][N:9]([C:14](=[O:36])[C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([O:22][C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[C:26]([O:32][CH3:33])=[C:25]([F:1])[CH:24]=2)=[C:17]([Cl:35])[CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of nitrosonium tetrafluoroborate (55 mg, 0.47 mmol) in dichloromethane (5 mL) was cooled to 0° C. and methyl-N-[3,5-dichloro-4-(3-amino-5-isopropyl-4-methoxyphenoxy)benzoyl]glycine (189 mg, 0.43 mmol) was added. The reaction mixture was further stirred at 0° C. for 1 h. Dichloromethane was removed from nitrogen and o-xylene (10 mL) was added to the reaction mixture. The reaction mixture was refluxed for 1 h and the solvent was removed. The crude reaction mixture was purified on column (silica gel, n-heptane/ethyl acetate, gradient elution from 98:2 to 60:40) to give 50 mg (26%) of methyl-N-[3,5-dichloro-4-(3-fluro-5-isopropyl-4-methoxyphenoxy)benzoyl]glycine.

Workup

customDichloromethane was removed from nitrogen and o-xylene (10 mL)
additionwas added to the reaction mixture
temperatureThe reaction mixture was refluxed for 1 h
customthe solvent was removed
customThe crude reaction mixture
customwas purified on column (silica gel, n-heptane/ethyl acetate, gradient elution from 98:2 to 60:40)

Sources & evidence

ORD record: ord-a587259a124244bc8aa06fdfcf9c8c2a
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153997B2

Reaction notes

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