Triethylamine → HCID 54375610, compound

HRID 1156126Notes

Reaction equation

HRID 1156126 reaction equation
FC(F)(F)C([N:5]([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][CH2:30][CH3:31])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[F:15])=O.C(N(CC)CC)C.C([O:43][C:44](=[O:48])[C@H:45]([CH3:47])[NH2:46])C>CCOCC>[F:15][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:6]=1[NH:5][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][CH2:30][CH3:31])[C:10]([NH:46][C@H:45]([C:44]([OH:48])=[O:43])[CH3:47])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76507L-Alanine ethyl esterHCID 20536442HCID 20536442, compound

Product 1

HCID 54375610HCID 54375610, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.75 g. of N-trifluoroacetyl-3-fluoro-4-(hexadecylamino)benzoyl chloride and 1.2 g. of triethylamine in 200 ml. of warm ether is treated with 1.55 g. alanine ethyl ester and refluxed for 24 hours. The hot solution is filtered, the residue is washed with hot ether, and the solution is evaporated. After treatment with aqueous methanolic potassium carbonate, the product is precipitated by acidification, filtered, and dried. Crystallization from acetone yields the N-[3-fluoro-4-(hexadecylamino)benzoyl]alanine as a white, crystalline solid.

Workup

  1. filtrationThe hot solution is filtered
  2. washthe residue is washed with hot ether
  3. customthe solution is evaporated
  4. customAfter treatment with aqueous methanolic potassium carbonate, the product is precipitated by acidification
  5. filtrationfiltered
  6. customdried
  7. customCrystallization from acetone

Sources & evidence

ORD record
ord-e1d49ebd4ec849fe9c0d9d7721064905
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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