Trifluoromethanesulfonic acid → benzyloxycarbonyl-beta-(allylamino)-L-alanine, methyl ester

HRID 260328Notes

Reaction equation

HRID 260328 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][NH2:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C(=N)O[CH2:23][CH:24]=[CH2:25].FC(F)(F)S(O)(=O)=O>C(Cl)Cl.C1CCCCC1.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:13][NH:14][CH2:25][CH:24]=[CH2:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 316905Allyl 2,2,2-TrichloroacetimidateHCID 110432213-Amino-N-((phenylmethoxy)carbonyl)-L-alanine methyl ester

Product 1

HCID 131719024benzyloxycarbonyl-beta-(allylamino)-L-alanine, methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

Dissolve Nα -(benzyloxycarbonyl)-β-(amino)-L-alanine, methyl ester (15.9 g, 63 mmol) in methylene chloride/cyclohexane (1:1, 600 mL). Add allyl trichloroacetimidate (26 g, 128 mmol) and trifluoromethanesulfonic acid (5 mL), 56.6 mmol). Stir at room temperature under a nitrogen atmosphere for 5 hours and dilute with methylene chloride. Wash with saturated aqueous sodium hydrogen carbonate, water, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give Nα -(benzyloxycarbonyl)-β-(allylamino)-L-alanine, methyl ester.

Workup

  1. washWash with saturated aqueous sodium hydrogen carbonate, water
  2. dry with materialdry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-48b5c45ebf184229b57afc64bc058b36
Source dataset
uspto-grants-1996_06
Patent number
US05527795

Reaction notes

Loading…