Bromine → 1-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-proline

HRID 903445Notes

Reaction equation

HRID 903445 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([CH2:8][CH2:9][C:10]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=[O:15])=[O:11])=[O:7])=[CH:4][CH:3]=1.[Br:22]Br>Br.C(O)(=O)C>[Br:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([CH:8]([Br:22])[CH2:9][C:10]([N:12]2[CH2:19][CH2:18][CH2:17][C@H:13]2[C:14]([OH:16])=[O:15])=[O:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 543439991-[3-(4-Bromobenzoyl)propionyl]-L-proline

Product 1

HCID 539233931-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-proline

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent3×

Procedure

To a solution of 17.7 g. of 1-[3-(4-bromobenzoyl)propionyl]-L-proline (Example 36) in 150 ml. of acetic acid is added dropwise, a solution of 9.0 g. of bromine in 20 ml. of acetic acid followed by 5 drops of hydrobromic acid in acetic acid. The mixture is stirred for 18 hours, evaporated to 1/2 its volume, poured into 300 ml. of ice water and extracted with methylene chloride. The organic extract is washed twice with water, once with saturated sodium chloride solution, dried over magnesium sulfate, clarified with charcoal and evaporated to dryness in vacuo. The desired product is recovered as 20.5 g. of a white amorphous solid.

Workup

  1. customevaporated to 1/2 its volume
  2. additionpoured into 300 ml
  3. extractionof ice water and extracted with methylene chloride
  4. extractionThe organic extract
  5. washis washed twice with water, once with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness in vacuo
  8. customThe desired product is recovered as 20.5 g

Sources & evidence

ORD record
ord-f1d896c0c23845089b36ca23322bd8bf
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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