Carbon Tetrachloride → 1-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-proline methyl ester

HRID 903442Notes

Reaction equation

HRID 903442 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:21])[CH2:10][CH2:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1.C(Cl)(Cl)(Cl)Cl.[Br:28]Br>Br.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:21])[CH2:10][CH:11]([C:12](=[O:20])[C:13]1[CH:14]=[CH:15][C:16]([Br:19])=[CH:17][CH:18]=1)[Br:28]

Participants

6

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 24408BromineHCID 228124471-[3-(4-Bromobenzoyl)propionyl]-L-proline methyl ester

Product 1

HCID 541386821-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-proline methyl ester

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3.52 g. of 1-[3-(4-bromobenzoyl)propionyl]-L-proline methyl ester (Example 29) in 50 ml. of carbon tetrachloride is added dropwise a solution of 0.51 ml. of bromine in 20 ml. of carbon tetrachloride. After 30 minutes 2 drops of 30% hydrobromic acid in acetic acid is added and the mixture is stirred at room temperature for 2 hours. The solvent is decanted from the resulting gum. The gum is dissolved in dichloromethane, washed twice with water, once with sodium chloride solution, dried over magnesium sulfate and clarified with charcoal. The filtrate is evaporated to dryness in vacuo giving the desired product as 3.87 g. of a gum.

Workup

  1. customThe solvent is decanted from the resulting gum
  2. dissolutionThe gum is dissolved in dichloromethane
  3. washwashed twice with water, once with sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe filtrate is evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-9021e47cabd5436aa5cbc7d4e6686cd5
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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