Boron tribromide → HCID 16065404, compound

HRID 2387692Notes

Reaction equation

B(Br)(Br)Br.[Cl:5][C:6]1[CH:37]=[CH:36][C:9]([O:10][CH:11]2[CH2:14][N:13]([C:15]([CH3:35])([CH3:34])[CH2:16][CH2:17][C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]([NH2:21])=[O:20])[CH2:12]2)=[CH:8][C:7]=1[O:38]C>ClCCl>[Cl:5][C:6]1[CH:37]=[CH:36][C:9]([O:10][CH:11]2[CH2:12][N:13]([C:15]([CH3:34])([CH3:35])[CH2:16][CH2:17][C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]([NH2:21])=[O:20])[CH2:14]2)=[CH:8][C:7]=1[OH:38]

Participants

Conditions

Temperature: 0 °C

Procedure

Boron tribromide (1M in dichloromethane, 1.75 mL, 1.75 mmol) was added to an ice-cooled solution of the product of example 113 (180 mg, 0.36 mmol) in dichloromethane (5 mL) and the mixture was stirred at 0° C. for 1.5 hour. The reaction was then quenched with 0.88 ammonia (30 mL) and the solution stirred at room temperature for 18 hours. The organic layer was separated, dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluting with dichloromethane to dichloromethane/methanol/0.88 ammonia (97:3:0.3), afforded the title compound as a colourless foam in 93% yield, 270 mg

Workup

customThe reaction was then quenched with 0.88 ammonia (30 mL)
stirringthe solution stirred at room temperature for 18 hours
customThe organic layer was separated
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customPurification of the residue by column chromatography on silica gel
washeluting with dichloromethane to dichloromethane/methanol/0.88 ammonia (97:3:0.3)

Sources & evidence

ORD record: ord-0380146f76a445c79ebcbda62a8324e9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268881B2

Reaction notes

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