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

HRID 2259226Notes

Reaction equation

HRID 2259226 reaction equation
O=[C:2]1C2C(=CC=CC=2)C(=O)N1C(CC1C=CC=CC=1)C(N[C@@H](CNCC=CC(=O)C(F)(F)F)C(OC)=O)=O.[CH2:39]([O:46][C:47]([NH:49][C@H:50]([C:53]([OH:55])=[O:54])[CH2:51][NH2:52])=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.S(=O)(=O)(O)O>CO.C(OCC)C>[CH2:39]([O:46][C:47]([NH:49][C@H:50]([C:53]([O:55][CH3:2])=[O:54])[CH2:51][NH2:52])=[O:48])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 2756313Z-Dap-OHHCID 131719215HCID 131719215, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

N-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-(S)-3-[(trifluoroacetyl-2-propenyl)amino]-2-amino-propionic acid, methyl ester 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-2408ea1c7b3746a3b08bd9ccc4c30fac
Source dataset
uspto-grants-1995_12
Patent number
US05472959

Reaction notes

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