Triethylamine → diethyl O-[4-(2-cyclohexylethylamino)phenylacetyl]tartrate

HRID 128338

Reaction equation

HRID 128338 reaction equation
FC(F)(F)C([N:5]([CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.[C:33]([CH:38]([CH:40]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[OH:41])[OH:39])([O:35][CH2:36][CH3:37])=[O:34]>CCOCC>[CH:18]1([CH2:17][CH2:16][NH:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:41][CH:40]([CH:38]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[OH:39])[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[O:14])=[CH:8][CH:7]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62333Butanedioic acid, 2,3-dihydroxy-, diethyl ester, S-(R*,R*)-HCID 204990254-[N-trifluoroacetyl-(2-cyclohexylethylamino)]phenylacetyl chloride

Product 1

HCID 20498970diethyl O-[4-(2-cyclohexylethylamino)phenylacetyl]tartrate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-[N-trifluoroacetyl-(2-cyclohexylethylamino)]phenylacetyl chloride and 1.2 g. triethylamine in 100 ml. warm ether is treated with 2.5 g. diethyl tartrate 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 diethyl O-[4-(2-cyclohexylethylamino)phenylacetyl]-tartrate 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-d6bcb04ee69c4d97b29d544f194fa0b0
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Linked notes

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