Acetic Acid → HCID 53902176, compound

HRID 903448Notes

Reaction equation

HRID 903448 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[Br:26]Br.O>ClCCl>[Br:26][CH:9]([C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][CH2:11][C:12]([N:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1[C:16]([OH:18])=[O:17])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 962WaterHCID 24408BromineHCID 53769121HCID 53769121, compound

Product 1

HCID 53902176HCID 53902176, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11.5 g. of 1-(4-benzoylbutyryl)-L-proline (Example 41) in 115 ml. of acetic acid is added dropwise a solution of 6.4 g. of bromine in 25 ml. of acetic acid. The mixture is stirred for 18 hours, reduced 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 in vacuo to a yellow gum. This gum is dissolved in dichloromethane, placed on a 11/2"×24" column of silica gel which has been wet with dichloromethane and eluted with ethyl acetate:acetic acid (1:1) taking 100 ml. cuts. Cut number 7 gives 2.1 g. of solid which is dissolved in dichloromethane, filtered through celite and evaporated to dryness giving the desired product as 2.0 g. of an orange gum.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washis washed with water and saline
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo to a yellow gum
  6. dissolutionThis gum is dissolved in dichloromethane
  7. washeluted with ethyl acetate:acetic acid (1:1)
  8. customgives 2.1 g
  9. filtrationfiltered through celite
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-3f3614e99769449590be8600a60b1997
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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