Hydrochloric Acid → HCID 68864220, compound

HRID 2109414Notes

Reaction equation

HRID 2109414 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[S:36](=[O:40])(=[O:39])[NH:37][CH3:38].[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[S:36](=[O:40])(=[O:39])[NH:37][CH3:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 68861873HCID 68861873, compound

Product 1

HCID 68864220HCID 68864220, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Boron tribromide (1 M dichloromethane solution; 2.37 ml) was added to a dichloromethane (10 ml) solution of the compound of Example 73 (0.40 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 methanol/ethyl acetate, thereby giving 0.29 g of the desired compound. Melting point: 119-120° C.

Workup

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

Sources & evidence

ORD record
ord-dfdd75cec846404b80227737762c2f36
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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