Boron tribromide → HCID 11517531, compound

HRID 1992842Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:27])[CH2:23][C:24]([OH:26])=[O:25])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12]C)=[CH:7][CH:6]=2.B(Br)(Br)Br>C(Cl)Cl>[OH:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:27])[CH2:23][C:24]([OH:26])=[O:25])=[CH:19][CH:20]=1)=[C:3]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:2]([CH3:1])=[CH:11]2

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 42 (75 mg, 0.17 mmol, 1 equiv) was dissolved in CH2Cl2 (5 mL) and cooled to 0° C. under N2. BBr3 (80 μL, 0.85 mmol, 5 equiv) was added dropwise and the resulting solution was allowed to stir at 0° C. for 2 h. The reaction mixture was then poured into ice and product extracted into EtOAc (250 mL). The organics were washed with saturated aqueous NaCl (100 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (0 to 100% CH3CN in water w/0.1% TFA) to provide the title compound (43) (22 mg, 30%) as a tan solid. 1HNMR (400 MHz, DMSO-d6): δ 10.66 (br s, 1H) 10.36 (br s, 1H), 7.87 (s, 1H), 7.57 (m, 1H), 7.32-7.15 (m, 9H), 6.56 (m, 2H), 2.52 (s, 2H), 2.21 (s, 3H). MS m/z 428.5 (M+H)+.

Workup

additionThe reaction mixture was then poured into ice and product
extractionextracted into EtOAc (250 mL)
washThe organics were washed with saturated aqueous NaCl (100 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by reverse phase HPLC (0 to 100% CH3CN in water w/0.1% TFA)

Sources & evidence

ORD record: ord-c1e2c0b86e784747ae8e1a68d8f34cd0
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07649093B2

Reaction notes

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