Triethylamine → HCID 53698438, compound

HRID 2057672Notes

Reaction equation

HRID 2057672 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][C:26]#[C:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[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:46][C:47](=[O:51])[C@H:48]([CH3:50])[NH2:49])C>CCOCC>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:27]#[C: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]2[CH:7]=[CH:8][C:9]([C:10]([NH:49][C@H:48]([C:47]([OH:51])=[O:46])[CH3:50])=[O:11])=[CH:13][CH:14]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76507L-Alanine ethyl esterHCID 20331208HCID 20331208, compound

Product 1

HCID 53698438HCID 53698438, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.75 g. of 4-[N-trifluoroacetyl-13-(4-chlorophenyl)tridec-12-ynylamino]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-{4-[13-(4-chlorophenyl)tridec-12-ynylamino]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-e39559c63e2547cdbef5107cbbbce0f0
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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