Boron tribromide → HCID 15293137, compound

HRID 2210797Notes

Reaction equation

HRID 2210797 reaction equation
B(Br)(Br)Br.[CH2:5]([S:7]([CH2:10][CH2:11][C:12]([NH:14][NH:15][C:16]([N:18]1[CH2:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[O:21][C:20]2[CH:29]=[CH:30][C:31]([O:33]C)=[CH:32][C:19]1=2)=[O:17])=[O:13])(=[O:9])=[O:8])[CH3:6]>>[CH2:5]([S:7]([CH2:10][CH2:11][C:12]([NH:14][NH:15][C:16]([N:18]1[CH2:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[O:21][C:20]2[CH:29]=[CH:30][C:31]([OH:33])=[CH:32][C:19]1=2)=[O:17])=[O:13])(=[O:9])=[O:8])[CH3:6]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 15293136HCID 15293136, compound

Product 1

HCID 15293137HCID 15293137, compound

Procedure

To a stirred solution of boron tribromide (1.0M in methylene chloride, 7.2 mL) at 5° C. (ice water bath) was added under nitrogen the title compound of Example 16 (e) (1.0 g). The ice bath was removed, and the reaction was stirred at room temperature for 3 hours. The reaction was carefully quenched by the addition of 1NNaOH (10 mL), acidified by the addition of 1NHCl (15 mL), and evaporated under vacuum. The resulting solid was triturated with water, and the insoluble material was collected by filtration, washed three times with water, and then with ethyl ether. Crystallization from ethanol (3A) yielded the title compound as white crystals. Mp: 191°-194° C.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was carefully quenched by the addition of 1NNaOH (10 mL)
  3. additionacidified by the addition of 1NHCl (15 mL)
  4. customevaporated under vacuum
  5. customThe resulting solid was triturated with water
  6. filtrationthe insoluble material was collected by filtration
  7. washwashed three times with water
  8. customCrystallization from ethanol (3A)

Sources & evidence

ORD record
ord-9f93177b40974a23bf1d4b97fc76a52b
Source dataset
uspto-grants-1995_10
Patent number
US05461046

Reaction notes

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