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

HRID 260327Notes

Reaction equation

HRID 260327 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:15]([OH:17])=[O:16])[CH2:13][NH2:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>C(OCC)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:15]([O:17][CH3:23])=[O:16])[CH2:13][NH2:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

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 -(benzyloxycarbonyl)-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 -(benzyloxycarbonyl)-β-(amino)-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-7f7c912e9ae042a090d1987b4d96404c
Source dataset
uspto-grants-1996_06
Patent number
US05527795

Reaction notes

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