Dichloromethane → HCID 91520096, compound

HRID 2109415Notes

Reaction equation

HRID 2109415 reaction equation
B(Br)(Br)Br.ClCCl.[O:8]1[CH:12]=[CH:11][C:10]([C:13]([N:15]([C:17]([C:19]2[O:20][CH:21]=[C:22]([C:32]3[CH:37]=[CH:36][C:35]([O:38]C)=[CH:34][CH:33]=3)[C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=2)=[O:18])[NH2:16])=[O:14])=[CH:9]1>O>[O:8]1[CH:12]=[CH:11][C:10]([C:13]([N:15]([C:17]([C:19]2[O:20][CH:21]=[C:22]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[C:23]=2[C:24]2[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=2)=[O:18])[NH2:16])=[O:14])=[CH:9]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 90979974HCID 90979974, compound

Product 1

HCID 91520096HCID 91520096, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Boron tribromide (1 M dichloromethane solution: 12.00 ml) was added dropwise to a dichloromethane (5 ml) solution of the compound of Example 84 (0.86 g) at 0° C., and stirred overnight at 25° C. After water was added to the reaction solution, the thus-precipitated crystals were filtered and purified by silica gel column chromatography (eluent: methanol/chloroform=1/9), thereby giving 0.40 g of the desired compound. Melting point: 168-172° C. (Recrystallized from ethyl acetate)

Workup

  1. filtrationthe thus-precipitated crystals were filtered
  2. custompurified by silica gel column chromatography (eluent: methanol/chloroform=1/9)

Sources & evidence

ORD record
ord-d157771898304dccaf9e6e9402454460
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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