Pyridine → N-[4-(hexadecylamino)benzoyl]-2-methylalanine

HRID 1980161Notes

Reaction equation

HRID 1980161 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].N1C=CC=CC=1.Cl.[CH2:15]([NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>O>[CH2:15]([NH:31][C:32]1[CH:33]=[CH:34][C:35]([C:36]([NH:1][C:2]([CH3:7])([C:3]([OH:5])=[O:4])[CH3:6])=[O:37])=[CH:39][CH:40]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6119Aminoisobutyric acidHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Product 1

HCID 20437359N-[4-(hexadecylamino)benzoyl]-2-methylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.24 g. of α-aminoisobutyric acid, 50 ml. of pyridine, and 25 ml. of H2O was stirred while 21.1 g. of 4-(hexadecylamino)benzoyl chloride hydrochloride was added. The mixture was stirred for 18 hours at ambient temperature and filtered. The filtrate was evaporated and the residual yellow glass was dissolved in 1N NaOH solution. The solution was extracted with diethyl ether and then acidified with 6N HCl. The precipitate was collected, dried, and recrystallized from acetone, melting point 199°-202° C.

Workup

  1. additionA mixture of 5.24 g
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. dissolutionthe residual yellow glass was dissolved in 1N NaOH solution
  5. extractionThe solution was extracted with diethyl ether
  6. customThe precipitate was collected
  7. customdried
  8. customrecrystallized from acetone, melting point 199°-202° C.

Sources & evidence

ORD record
ord-b1efaf5be7ff49edab73a62b7edbcb0b
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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