L-Methionine → N(4-aminobenzoyl)-L-methionine

HRID 488098

Reaction equation

HRID 488098 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>C1C=CC=CC=1.C(N(CC)CC)C>[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:16])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 6137L-MethionineHCID 177720Benzoyl chloride, 4-amino-

Product 1

HCID 22851148N(4-aminobenzoyl)-L-methionine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

In an Erlenmeyer flask, 1.35 g of para-aminobenzoic acid chloride are dissolved in 20 ml benzene in the presence of 2.8 ml triethylamine. 1.49 g L-methionine is added progressively and the resultant mixture is filtered. After evaporation of the filtrate to dryness under vacuum (15 mm Hg), the residue is dissolved in N hydrochloric acid and extracted with chloroform. The chloroformic solution is successively washed with several ml of 10% aqueous HKCO3 solution and with water. It is then collected, dried over magnesium sulfate and evaporated. The product obtained is precipitated in cyclohexane and filtered. After recrystallization in a (1:1) mixture of 95 alcohol-water, 1.95 g of white crystals are isolated. M.p.: 172° C.

Workup

  1. filtrationthe resultant mixture is filtered
  2. customAfter evaporation of the filtrate to dryness under vacuum (15 mm Hg)
  3. dissolutionthe residue is dissolved in N hydrochloric acid
  4. extractionextracted with chloroform
  5. washThe chloroformic solution is successively washed with several ml of 10% aqueous HKCO3 solution and with water
  6. customIt is then collected
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe product obtained
  10. customis precipitated in cyclohexane
  11. filtrationfiltered
  12. customAfter recrystallization
  13. additionin a (1:1) mixture of 95 alcohol-water, 1.95 g of white crystals
  14. customare isolated

Sources & evidence

ORD record
ord-197240ff4471474cbc02312e932c5995
Source dataset
uspto-grants-1994_03
Patent number
US05298647

Linked notes

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