Boron tribromide → HCID 16041608, compound

HRID 418622Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:27][C:28](=[O:39])[CH2:29][C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]=[CH:20][N:21]([CH2:23][CH2:24][O:25]C)[CH:22]=3)[S:17][C:10]=12.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:27][C:28](=[O:39])[CH2:29][C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]=[CH:20][N:21]([CH2:23][CH2:24][OH:25])[CH:22]=3)[S:17][C:10]=12

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 91 (85 mg, 0.156 mmol) in dry DCM (2 mL) was added, at −78° C., BBr3 (0.6 mL, 4 eq, 0.62 mmol, 1M soln in DCM) and the reaction mixture was slowly warmed to 0° C. and allowed to stir at 0° C. for 30 mins. The reaction mixture was quenched with MeOH and the solvents were removed under reduced pressure. Purification by column chromatography (Gilson, 25% MeOH in water to 75% MeOH in water) afforded title compound 89 (26 mg, 27% yield). MS (m/z): 532.1 (M+H).

Workup

customThe reaction mixture was quenched with MeOH
customthe solvents were removed under reduced pressure
customPurification by column chromatography (Gilson, 25% MeOH in water to 75% MeOH in water)

Sources & evidence

ORD record: ord-4844fc837be846be981f2e186dcd2842
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093264B2

Reaction notes

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