Methanol → HCID 86746647, compound

HRID 1614049Notes

Reaction equation

HRID 1614049 reaction equation
[CH3:1]O.S(Cl)([Cl:5])=O.[NH2:7][C@@H:8]([C:13]([OH:15])=[O:14])[CH2:9][C:10]([OH:12])=[O:11]>C(OCC)C>[ClH:5].[CH3:1][CH:9]([C:10]([OH:12])=[O:11])[C@H:8]([C:13]([OH:15])=[O:14])[NH2:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 83887D-Aspartic Acid

Product 1

HCID 86746647HCID 86746647, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cool methanol (525 mL) to -20° C. and place under an atmosphere of nitrogen. Add, by dropwise addition, thionyl chloride (80 mL). Add D-aspartic acid (100 g, 0.75 mol) in one portion and allow the reaction to warm to room temperature over approximately 1 hour. Stir for 50 minutes at room temperature and pour into anhydrous ethyl ether (1.5 L). Filter the resulting solid, dissolve partly in warm ethanol (500 mL) and filter again. Add the filtrated to ethyl ether (1.5 L) and filter the resulting solid. Dry to give the title compound (85.3 g, 62%).

Workup

  1. customthe reaction
  2. filtrationFilter the resulting solid
  3. dissolutiondissolve partly in warm ethanol (500 mL)
  4. filtrationfilter again
  5. additionAdd the
  6. filtrationfiltrated to ethyl ether (1.5 L)
  7. filtrationfilter the resulting solid
  8. customDry

Sources & evidence

ORD record
ord-6c25439bd71f414ba33c87d695474b27
Source dataset
uspto-grants-1993_03
Patent number
US05194430

Reaction notes

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