Water → HCID 22733874, compound

HRID 1057905Notes

Reaction equation

[C:1]([C:9]1[O:10][C:11]2[C:17]([O:18]C)=[CH:16][CH:15]=[C:14]([C:20]([NH:22][C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])=[O:21])[C:12]=2[CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.O>ClCCl>[C:1]([C:9]1[O:10][C:11]2[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([C:20]([NH:22][C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])=[O:21])[C:12]=2[CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Under a nitrogen atmosphere, Compound 168 (0. 04 g) obtained in Example 168 was dissolved in dry dichloromethane (2 ml) and the solution was cooled to −78° C. A 2.4M solution (0.125 ml) of boron tribromide in dichloromethane was slowly and dropwise added to the solution, and then the mixture was warmed to the room temperature and stirred one night. Distilled water (5 ml) was added to the mixture followed by stirring for one hour. The reaction solution was extracted with chloroform, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give Compound 169 (0.02 g, 46.9%) as a pale-yellow solid.

Workup

additiondropwise added to the solution
temperaturethe mixture was warmed to the room temperature
stirringby stirring for one hour
extractionThe reaction solution was extracted with chloroform
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a18cf6d446dd4e439ce785a33a13c1e5
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514996B2

Reaction notes

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