Triethylamine → HCID 20503628, compound

HRID 850985Notes

Reaction equation

HRID 850985 reaction equation
FC(F)(F)C([N:5]([C:22]1[CH:23]=[C:24]([C:27](Cl)=[O:28])[S:25][CH:26]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=O.C(N(CC)CC)C.[C:39]([O:50][CH2:51][CH3:52])(=[O:49])[CH:40]([CH:42]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[OH:43])[OH:41]>CCOCC>[CH2:6]([NH:5][C:22]1[CH:23]=[C:24]([C:27]([O:41][CH:40]([CH:42]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[OH:43])[C:39]([O:50][CH2:51][CH3:52])=[O:49])=[O:28])[S:25][CH:26]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 20503600HCID 20503600, compound

Product 1

HCID 20503628HCID 20503628, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-[N-(trifluoroacetyl)-N-(hexadecyl)amino]-2-thiophenecarbonyl chloride and 1.2 g. of triethylamine in 100 ml. of warm ether is treated with 2.5 g. of 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 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-4cd3b7f2a26f46f5b18f44ce024da93f
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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