Hydrochloric Acid → HCID 68861801, compound

HRID 2109412Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:35]=[CH:34][C:10]([C:11]([NH:13][NH:14][C:15]([C:17]2[O:18][CH:19]=[C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:16])=[O:12])=[CH:9][C:8]=1[NH:36][S:37]([CH3:40])(=[O:39])=[O:38].[OH-].[Na+].Cl>C(Cl)(Cl)Cl.ClCCl>[OH:6][C:7]1[CH:35]=[CH:34][C:10]([C:11]([NH:13][NH:14][C:15]([C:17]2[O:18][CH:19]=[C:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:21]=2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:16])=[O:12])=[CH:9][C:8]=1[NH:36][S:37]([CH3:40])(=[O:39])=[O:38]

Participants

Conditions

Temperature: 25 °C

Procedure

Boron tribromide (1 M dichloromethane solution; 5.10 ml) was added to a dichloromethane (10 ml) solution of the compound of Example 70 (0.86 g) at 0° C. and stirred at 25° C. for 3 hours. The reaction solution was mixed with 2 M aqueous sodium hydroxide solution, stirred for 0.3 hours, and mixed with 2 M hydrochloric acid and chloroform. The organic layer was washed with saturated brine and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: 0→15% methanol/chloroform gradient) and recrystallized from isopropyl alcohol, thereby giving 0.29 g of the desired compound. Melting point: 230-231° C.

Workup

stirringstirred for 0.3 hours
washThe organic layer was washed with saturated brine
dry with materialdried over MgSO4
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (eluent: 0→15% methanol/chloroform gradient)
customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record: ord-3dfbf8cd5e6e45918e5e2548e3beba64
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514452B2

Reaction notes

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