L-Aspartic Acid → HCID 22842245, compound

HRID 1647035Notes

Reaction equation

HRID 1647035 reaction equation
CO[C:3](=[S:11])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[NH2:12][C@H:13]([C:18]([OH:20])=[O:19])[CH2:14][C:15]([OH:17])=[O:16].[OH-].[Na+]>CCOCC>[Cl:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([NH:12][C@H:13]([C:18]([OH:20])=[O:19])[CH2:14][C:15]([OH:17])=[O:16])=[S:11])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 5960L-Aspartic AcidHCID 14798Sodium HydroxideHCID 15329824HCID 15329824, compound

Product 1

HCID 22842245HCID 22842245, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl-4-chlorothiobenzoate (2.11 g, 11.3 mmol), aspartic acid (2.7 g, 2.02 mmol), aq NaOH (3N, 8.8 ml), and Et2O (8 ml) were vigourously stirred at room temperature for 3 days. The aq. layer was separated, acidified (dil.HCl), and extracted with Et2O (2×25 ml). The combined ether extracts were dried (MgSO4), filtered, and concentrated under reduced pressure to yield N-p-chlorothiobenzoylaspartic acid (0.23 g).

Workup

  1. customThe aq. layer was separated
  2. extractionextracted with Et2O (2×25 ml)
  3. dry with materialThe combined ether extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94768223596f43cca5a8b8212daa2d0a
Source dataset
uspto-grants-1993_01
Patent number
US05182402

Reaction notes

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