Triethylamine → HCID 20549366, compound

HRID 2058760Notes

Reaction equation

HRID 2058760 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:43]([O:54][CH2:55][CH3:56])(=[O:53])[CH:44]([CH:46]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[OH:47])[OH:45]>CCOCC>[F:31][C:30]([F:32])([F:33])[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:14]=[CH:13][C:9]([C:10]([O:45][CH:44]([CH:46]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[OH:47])[C:43]([O:54][CH2:55][CH3:56])=[O:53])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 20549315HCID 20549315, compound

Product 1

HCID 20549366HCID 20549366, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-[N-trifluoroacetyl-15-(trifluoromethyl)pentadecylamino)benzoyl chloride and 1.2 g. triethylamine in 100 ml. warm ether is treated with 2.5 g. diethyl tartarate 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-25051856dad747d38941e7e81eaf6592
Source dataset
uspto-grants-1982_03
Patent number
US04318914

Reaction notes

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