Methanol → 3-Amino-N-((phenylmethoxy)carbonyl)-L-alanine methyl ester

HRID 22528Notes

Reaction equation

HRID 22528 reaction equation
[C:1]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][NH2:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].S(=O)(=O)(O)O.[CH3:23]O>C(OCC)C>[C:1]([NH:11][C@H:12]([C:15]([O:17][CH3:23])=[O:16])[CH2:13][NH2:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2756313Z-Dap-OH

Product 1

HCID 110432213-Amino-N-((phenylmethoxy)carbonyl)-L-alanine methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve Nα-(carbobenzyloxy)-β-(amino)-L-alanine (47.6 g, 0.2 mol) in methanol (500 mL) and treat with concentrated sulfuric acid (0.5 mL). Heat to 60° C. for 16 hours, cool and reduce the solvent by 50% in vacuo. Dilute with ethyl ether (500 mL), wash with saturated sodium hydrogen carbonate, then brine. Dry (MgSO4) and evaporate the solvent in vacuo to give Nα-(carbobenzyloxy)-β-(amino)-L-alanine, methyl ester. Dissolve Nα-(carbobenzyloxy)-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-(carbobenzyloxyl)-β-(allylamino)-L-alanine, methyl ester.

Workup

  1. temperaturecool
  2. washwash with saturated sodium hydrogen carbonate
  3. dry with materialDry (MgSO4)
  4. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-527b983b5852440c80ee5f7d8ac1e9b7
Source dataset
uspto-grants-1995_06
Patent number
US05428158

Reaction notes

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