Diethyl Ether → Hydrochloric Acid

HRID 1035319Notes

Reaction equation

HRID 1035319 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].S(Cl)([Cl:12])=O.[CH2:14](OCC)C>CO>[NH2:1][C@H:2]([CH2:3][C:4]([O:6][CH3:14])=[O:5])[C:7]([OH:9])=[O:8].[ClH:12]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl Chloride2×HCID 83887D-Aspartic Acid

Product 2

HCID 313Hydrochloric AcidHCID 642249HCID 642249, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution n of D-aspartic acid (25 g, 187.8 mmol) suspended in methanol (125 mL) at 0° C. was added thionyl chloride (13.7 mL, 187.8 mmol) dropwise. After addition of the thionyl chloride, the solution was allowed to warm to ambient temperature. The reaction mixture was concentrated until a precipitate began to form and then diethyl ether (700 mL) was added. The mixture was stirred for 30 minutes. The precipitate was collected by filtration to afforded the title compound as an HCl salt.

Workup

  1. concentrationThe reaction mixture was concentrated until a precipitate
  2. customto form
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-91cc34c355d8441ab275812de619339a
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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