Bromine → HCID 53886994, compound

HRID 903438Notes

Reaction equation

HRID 903438 reaction equation
[C:1]([CH2:9][CH2:10][C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21]Br>Br.C(O)(=O)C>[Br:21][CH:9]([C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][C:11]([N:13]1[CH2:20][CH2:19][CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])=[O:12]

Participants

5

Reactant 2

HCID 24408BromineHCID 53988049HCID 53988049, compound

Product 1

HCID 53886994HCID 53886994, compound

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 176Acetic AcidSolvent3×

Procedure

To a solution of 8.25 g. of 1-(3-benzoylpropionyl)-L-proline (Example 16) in 80 ml. of acetic acid is added 5 drops of 30% hydrogen bromide in acetic acid followed by 4.80 g. of bromine in 20 ml. of acetic acid. The mixture is stirred at room temperature for 18 hours, evaporated to 1/3 its volume, poured into ice and water and extracted with dichloromethane. The organic extract is washed with water and saline, dried over magnesium sulfate and evaporated to dryness giving the desired product as 10.3 g. of a white glass.

Workup

  1. customevaporated to 1/3 its volume
  2. additionpoured into ice and water
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washis washed with water and saline
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-ba8d6e6112f5494db4c42392c154719b
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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