Triethylamine → HCID 54316648, compound

HRID 904264Notes

Reaction equation

HRID 904264 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]([O:32][CH3:33])=[O: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>[C:30]([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)([O:32][CH3:33])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76507L-Alanine ethyl esterHCID 21163361HCID 21163361, compound

Product 1

HCID 54316648HCID 54316648, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.75 g. of N-trifluoroacetyl-4-(15-carbomethoxypentadecylamino)benzoyl chloride and 1.2 g. of triethylamine in 20 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-01483073d5e945fabbeded999ec47f88
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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