Allyl bromide → HCID 131711766, compound

HRID 1395664Notes

Reaction equation

HRID 1395664 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH2:20](Br)[CH:21]=[CH2:22]>CO>[NH:1]([CH2:22][CH:21]=[CH2:20])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([O:18][CH3:19])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 131711767HCID 131711767, compound

Product 1

HCID 131711766HCID 131711766, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

533 Mg. (2 meq.) of H-Tyr-D-Ala-OMe in 80 ml. of methanol with 400 mg. (4 meq.) of powdered KHCl3 and 484 mg. (4 meq.) of allyl bromide were refluxed 2.5 hours under nitrogen. The solution was evaporated to dryness and dried in vacuo over KOH. The desired product was purified by high performance liquid chromatography using reverse phase C-18 column and eluting with 0.1 molar NH4OAc ph 4.2 containing 23% acetonitrile. The mass spectrometric analysis of the isolated product confirms the presence of an N-allyl group on the dipeptide. TLC (S. C., BAW peptidechlorine spray) indicated the presence of one major component RF 0.65.

Workup

  1. customThe solution was evaporated to dryness
  2. dry with materialdried in vacuo over KOH
  3. customThe desired product was purified by high performance liquid chromatography
  4. washeluting with 0.1 molar NH4OAc ph 4.2 containing 23% acetonitrile

Sources & evidence

ORD record
ord-1f072fe6dcd840c5af64c5e53999d1d1
Source dataset
uspto-grants-1980_05
Patent number
US04205069

Reaction notes

Loading…