Triethylamine → HCID 22811159, compound

HRID 1395725Notes

Reaction equation

HRID 1395725 reaction equation
FC(F)(F)C([N:5]([CH2:15][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][C:30]([F:33])([F:32])[F:31])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.C([O:45][C:46](=[O:50])[C@H:47]([CH3:49])[NH2:48])C>CCOCC>[F:33][C:30]([F:31])([F:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:48][C@H:47]([C:46]([OH:50])=[O:45])[CH3:49])=[O:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76507L-Alanine ethyl esterHCID 20549315HCID 20549315, compound

Product 1

HCID 22811159HCID 22811159, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.75 g. of 4-[N-trifluoroacetyl-15-(trifluoromethyl)pentadecylamino]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 product 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
  8. customyields the product as a white, crystalline solid

Sources & evidence

ORD record
ord-738ede2bfc4a4ac4bac3c60df98aca8a
Source dataset
uspto-grants-1980_05
Patent number
US04205085

Reaction notes

Loading…