Water → HCID 12044589, compound

HRID 1840618Notes

Reaction equation

B(Br)(Br)Br.[CH3:5][C:6]1([CH3:46])[C:10](=[O:11])[N:9]([C@@H:12]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[C:13]([NH:15][C@H:16]([CH3:20])[CH2:17][CH2:18][OH:19])=[O:14])[C:8](=[O:25])[N:7]1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[CH3:43])=[O:35])=[C:29]([O:44]C)[CH:28]=1.O>ClCCl>[CH3:46][C:6]1([CH3:5])[C:10](=[O:11])[N:9]([C@@H:12]([CH2:21][CH:22]2[CH2:24][CH2:23]2)[C:13]([NH:15][C@H:16]([CH3:20])[CH2:17][CH2:18][OH:19])=[O:14])[C:8](=[O:25])[N:7]1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[CH3:43])=[O:35])=[C:29]([OH:44])[CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

488 μL of boron tribromide were added under argon to a solution of 220 mg (0.39 mmol) of the compound of Example 3 in 40 mL of absolute dichloromethane at −78° C. and the reaction mixture was allowed to warm to 0° C. with ice cooling. After 30 minutes at 0° C., water was cautiously added. The phases were separated, and the organic phase was washed four times with water and dried over sodium sulfate. After filtration, removal of the solvent in vacuo, chromatographic purification by preparative HPLC and freeze drying of the product fractions, 81 mg (37%) of the title compound were obtained.

Workup

customThe phases were separated
washthe organic phase was washed four times with water
dry with materialdried over sodium sulfate
filtrationAfter filtration, removal of the solvent
customin vacuo, chromatographic purification by preparative HPLC
customfreeze drying of the product fractions

Sources & evidence

ORD record: ord-466bea21ea7e4f2b8e3db269e4d9212e
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680333B2

Reaction notes

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