Allyl bromide → HCID 131713321, compound

HRID 905094Notes

Reaction equation

HRID 905094 reaction equation
[NH2:1][C@H:2]([C:15]([NH:17][CH2:18][C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+].[CH2:54](Br)[CH:55]=[CH2:56]>C(O)C>[NH:1]([CH2:56][CH:55]=[CH2:54])[C@H:2]([C:15]([NH:17][CH2:18][C:19]([NH:21][CH2:22][C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:42]([O:44][C:45]([CH3:46])([CH3:47])[CH3:48])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])=[O:20])=[O:16])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 131713322HCID 131713322, compound

Product 1

HCID 131713321HCID 131713321, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

H-Tyr(But)-Gly-Gly-Phe-Leu-OBut (2.0 g., 3 mM) was dissolved in ethanol (90 ml.). To the solution were added sodium bicarbonate (0.378 g., 4.5 mM) and allyl bromide (0.387 ml., 4.5 mM). The solution was stirred and refluxed for 20 hours. The solvent was then evaporated in vacuo and the residue dissolved in a mixture of ethyl acetate (120 ml.) and water (80 ml.). The two phases were separated and the organic phase was washed with saturated brine (80 ml.) and dried (Na2SO4). The solvent was evaporated in vacuo to give a gum-like residue which was chromatographed using the dry column chromatography technique with ethyl acetate/methanol 90:10 v/v as eluent. The product band was eluted from the column with ethyl acetate/methanol 85:15 v/v. The solvent was evaporated in vacuo from the eluate to give allyl-Tyr(But)-Gly-Gly-Phe-Leu-OBut having Rf 0.48 (t.l.c. on silica gel; ethyl acetate/methanol 90:10 v/v).

Workup

  1. temperaturerefluxed for 20 hours
  2. customThe solvent was then evaporated in vacuo
  3. dissolutionthe residue dissolved in a mixture of ethyl acetate (120 ml.) and water (80 ml.)
  4. customThe two phases were separated
  5. washthe organic phase was washed with saturated brine (80 ml.)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated in vacuo
  8. customto give a gum-like residue which
  9. customwas chromatographed
  10. washThe product band was eluted from the column with ethyl acetate/methanol 85:15 v/v
  11. customThe solvent was evaporated in vacuo from the eluate

Sources & evidence

ORD record
ord-30a062b115a449fab7e182944d72768a
Source dataset
uspto-grants-1983_12
Patent number
US04421744

Reaction notes

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