L-Lysine → HCID 67924379, compound

HRID 1084823Notes

Reaction equation

HRID 1084823 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9].[NH2:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26]>O1CCCC1.O>[NH2:20][C@H:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9]

Participants

5

Reactant 2

HCID 5962L-LysineHCID 3063368HCID 3063368, compound

Product 1

HCID 67924379HCID 67924379, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-(2-thienyl)acrylamido]benzoic acid (500 mg, 1.8 mmol) in tetrahydrofuran (5 ml) was added L-lysine (267 mg, 1.8 mmol) dissolved in water (3 ml). After stirring the mixture at room temperature for 1.5 hour, the solvent was removed, and the residue was triturated with ether to give crystals. After filtering and drying, the crystals were dissolved in water, the insoluble matter was removed and water was distilled off. The residue was crystallized with ether to give pale yellow solids of the desired L-lysine salt (510 mg, yield, 66%). m.p., 208°-213° C.

Workup

  1. customthe solvent was removed
  2. customthe residue was triturated with ether
  3. customto give crystals
  4. filtrationAfter filtering
  5. customdrying
  6. dissolutionthe crystals were dissolved in water
  7. customthe insoluble matter was removed
  8. distillationwater was distilled off
  9. customThe residue was crystallized with ether

Sources & evidence

ORD record
ord-ec83b9e36015448fbdc19cee50eb30e7
Source dataset
uspto-grants-1991_04
Patent number
US05006548

Reaction notes

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