Dichloromethane → HCID 53887193, compound

HRID 1870819Notes

Reaction equation

HRID 1870819 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[CH:14]=[C:13]([N:15]=[C:16]([NH2:23])[N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[O:12][N:11]=2)[CH3:9])[CH:5]=[CH:4][C:3]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=1.C(Cl)Cl.B(Br)(Br)Br.[OH-].[Na+]>O1CCCC1>[NH2:23][C:16]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[N:15][C:13]1[O:12][N:11]=[C:10]([CH:8]([C:6]2[CH:5]=[CH:4][C:3]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)=[C:2]([F:1])[CH:7]=2)[CH3:9])[CH:14]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 54085864HCID 54085864, compound

Product 1

HCID 53887193HCID 53887193, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (5.16 g) obtained in Example 63 was dissolved in tetrahydrofuran (100 ml) under a nitrogen atmosphere and then a methylene chloride solution (40 ml) of boron tribromide (1.6 ml) was added at -78° C., after which the temperature was elevated to room temperature over one hour and the stirring was further conducted at room temperature for 3 hours. The reaction mixture was neutralized with a 15% aqueous sodium hydroxide solution and then subjected to extraction with ethyl acetate and methanol. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (chloroform alone→chloroform/methanol=50/1→33/1) to obtain the desired compound (2.67 g).

Workup

  1. waitthe stirring was further conducted at room temperature for 3 hours
  2. extractionsubjected to extraction with ethyl acetate and methanol
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (chloroform alone→chloroform/methanol=50/1→33/1)

Sources & evidence

ORD record
ord-ff29cbf0e92e4abfbd75d547ece77a02
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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