Hydrogen Bromide → HCID 18538605, compound

HRID 412934Notes

Reaction equation

HRID 412934 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([N:19]([CH2:28][CH2:29][CH2:30][N:31]2[CH2:36][CH2:35][CH:34]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:33][CH2:32]2)[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)=[O:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.Br.C(OCC)C>C(O)(=O)C>[CH2:37]([CH:34]1[CH2:35][CH2:36][N:31]([CH2:30][CH2:29][CH2:28][N:19]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C:17]([CH:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)=[O:18])[CH2:32][CH2:33]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 18538871HCID 18538871, compound

Product 1

HCID 18538605HCID 18538605, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

The compound obtained in Example 65 (4.89 g, 7.85 mmol) was dissolved in acetic acid (5 ml). To the solution was added 30% solution of hydrogen bromide in acetic acid (15 ml), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added diethylether (60 ml), and supernatant solution was removed by decantation. To the residure was added diethylether (60 ml), and supernatant solution was removed by decantation. These procedure was repeated further three times. To the residue was added aqueous solution of 1N-sodium hydroxide (50 ml) and the mixture was extracted with dichloromethane (80 ml, 30 ml×2). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was subjected to column chromatography (alumina 200 g, ethyl acetate/methanol=1/0 to 4/1 to 1/1), and the desired fraction was concentrated under reduced pressure to give the titled compound (3.18 g, 6.51 mmol, Yield 83%) as pale brown oily substance.

Workup

  1. customwas removed by decantation
  2. additionTo the residure was added diethylether (60 ml), and supernatant solution
  3. customwas removed by decantation
  4. additionTo the residue was added aqueous solution of 1N-sodium hydroxide (50 ml)
  5. extractionthe mixture was extracted with dichloromethane (80 ml, 30 ml×2)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. concentrationthe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e0b9fda52f074c0e85d34c7421ab7b0f
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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