Methanol → HCID 69440601, compound

HRID 404913Notes

Reaction equation

C[O:2][C:3]1[CH:25]=[CH:24][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:17]=[C:16]([CH:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])[O:15][N:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:17]=[C:16]([CH:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])[O:15][N:14]=3)=[CH:11][N:12]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of Example 53B (726 mg, 2.02 mmol) in dichloromethane (20 mL) was added boron tribromide (763 μL, 8.08 mmol) at −78° C. Upon addition, the mixture was allowed to stir at 25° C. for 16 hours. The reaction was then cooled to 0° C., treated with methanol (10 mL) and diluted with dichloromethane (80 mL). The resulting mixture was washed with water (120 mL) and brine (150 mL). The organic layer was dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 40% to 90% ethyl acetate in hexanes to provide 384 mg of the title compound (55%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.41 (d, J=6.99 Hz, 3H) 1.87 (s, 3H) 4.93-5.24 (m, 1H) 6.55 (s, 1H) 6.82-6.95 (m, 2H) 7.16-7.34 (m, 2H) 7.95 (s, 1H) 8.53 (d, J=8.09 Hz, 1H) 11.78 (s, 1H); MS (ESI) m/z 346.0 (M+H)+.

Workup

additionUpon addition
temperatureThe reaction was then cooled to 0° C.
washThe resulting mixture was washed with water (120 mL) and brine (150 mL)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 40% to 90% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-021392a0d835486baa2e903c6318063b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748627B2

Reaction notes

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