Hexane → HCID 53661366, compound

HRID 1492406Notes

Reaction equation

HRID 1492406 reaction equation
[CH:1]12[CH2:9][CH:5]3[CH2:6][CH:7]([CH2:8]1)[C:3]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[CH:19]([C:28]1[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=1)[C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)=[O:12])([CH2:4]3)[CH2:2]2.CCCCCC.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]12[CH2:9][CH:5]3[CH2:6][CH:7]([CH2:8]1)[C:3]([NH:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[CH:19]([C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:12])([CH2:4]3)[CH2:2]2

Participants

6

Reactant 4

HCID 8058HexaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 53910045HCID 53910045, compound

Product 1

HCID 53661366HCID 53661366, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 40 ml of methylene chloride was dissolved 2.5 g of Compound 1 obtained in Example 1, and the solution was cooled to from -5° to -15° C. Then, 20 ml of a hexane solution containing 1M boron tribromide was added thereto. The mixture was stirred at room temperature for two hours and thirty minutes. The reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 0.63 g of the desired compound as a solid.

Workup

  1. temperaturethe solution was cooled to from -5° to -15° C
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-741c5afad6f54f8b988a6852f4d989f4
Source dataset
uspto-grants-1994_12
Patent number
US05374634

Reaction notes

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