Lactic Acid → 1-Carboxyethyl 4-(2-cyclohexylethylamino)phenylacetate

HRID 2166783Notes

Reaction equation

HRID 2166783 reaction equation
[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]([OH:25])(=[O:24])[CH:21]([CH3:23])O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[CH:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH:21]([C:20]([OH:25])=[O:24])[CH3:23])=[O:18])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 612Lactic AcidHCID 69252-Methylbenzenesulfonic acidHCID 204989854-(2-Cyclohexylethylamino)phenylacetic acid

Product 1

HCID 204989661-Carboxyethyl 4-(2-cyclohexylethylamino)phenylacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A flask containing 10.0 g. 4-(2-cyclohexylethylamino)phenylacetic acid, 3.3 g. lactic acid, 500 mg. toluenesulfonic acid and 500 ml. toluene equipped with a Soxhlet extractor charged with activated 4 A Linde molecular sieves. The solution is refluxed for 24 hours during which time the Soxhlet extractor is charged twice more with fresh sieves. The hot solution is filtered and left to cool, whereupon 1-carboxyethyl 4-(2-cyclohexylethylamino)phenylacetate separates as off-white crystals.

Workup

  1. additionA flask containing 10.0 g
  2. additioncharged
  3. temperatureThe solution is refluxed for 24 hours during which time the Soxhlet extractor
  4. additionis charged twice more with fresh sieves
  5. filtrationThe hot solution is filtered
  6. waitleft
  7. temperatureto cool, whereupon 1-carboxyethyl 4-(2-cyclohexylethylamino)phenylacetate

Sources & evidence

ORD record
ord-8d82bec79b614671baf3ccf1317ba36d
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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