Carbon tetrabromide → HCID 22709907, compound

HRID 352817Notes

Reaction equation

HRID 352817 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:28][CH2:29]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:32][CH2:29][CH2:28][CH:9]1[CH2:10][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 24437Sodium SulfiteHCID 22709724HCID 22709724, compound

Product 1

HCID 22709907HCID 22709907, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (50 ml) was dissolved 1-(tert-butoxycarbonyl)-4-[(6-chloronaphthalen-2-yl)sulfonyl]-2-(2-hydroxylethyl)piperazine (1.00 g), followed by the addition of carbon tetrabromide (1.46 g) and triphenylphosphine (1.15 g). The resulting mixture was stirred at room temperature for 30 minutes. After the addition of a saturated aqueous solution of sodium sulfite, the organic layer was collected from the mixture. The organic layer was dried over anhydrous sodium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column [hexane:ethyl acetate=10:1 to 6:1], whereby the title compound (990 mg) was obtained as a colorless foam.

Workup

  1. customthe organic layer was collected from the mixture
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by chromatography on a silica gel column [hexane:ethyl acetate=10:1 to 6:1], whereby the title compound (990 mg)
  6. customwas obtained as a colorless foam

Sources & evidence

ORD record
ord-44b729efe875465ea374123b4836abbb
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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