Water → Ethyl 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-5,5-dimethyl-4-oxo-2-thiazolidinyl]propyl}benzoate

HRID 28216

Reaktionsgleichung

Reaktionsgleichung von HRID 28216
O=[CH:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[NH2:17][CH2:18][CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[SH:27][C:28]([CH3:33])([CH3:32])[C:29](O)=[O:30].O>C1(C)C=CC=CC=1>[OH:26][C:20]1([CH2:19][CH2:18][N:17]2[C:29](=[O:30])[C:28]([CH3:33])([CH3:32])[S:27][CH:2]2[CH2:3][CH2:4][CH2:5][C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 784212-Mercapto-2-methylpropanoic acidHCID 12897183Ethyl 4-(4-oxobutyl)benzoateHCID 133714841-(2-Aminoethyl)cyclohexanol

Produkt 1

HCID 23339601Ethyl 4-{3-[3-[2-(1-Hydroxycyclohexyl)ethyl]-5,5-dimethyl-4-oxo-2-thiazolidinyl]propyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-(4-oxobutyl)benzoate (5.5 g., 0.025 mole) and 1-(2-aminoethyl)cyclohexanol (3.7 g., 0.026 mole) in toluene (40 ml.) is boiled in an open flask for 5 minutes to remove the formed water as the azeotrope. 2-Mercapto-2-methylpropionic acid (3.3 g., 0.0275 mole) is added and the solution is boiled under a Dean-Stark water separator for 5 hours. The solution is then cooled, washed with 2 N hydrochloric acid and water, and dried over sodium sulfate. The solvent is removed at reduced pressure. The residue is chromatographed on 165 g. of silica gel with 2% methanol in chloroform as the eluent. There is obtained 4.6 g. of the title ester as a light yellow, viscous oil.

Aufarbeitung

  1. customto remove the formed water as the azeotrope
  2. temperatureThe solution is then cooled
  3. washwashed with 2 N hydrochloric acid and water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed at reduced pressure
  6. customThe residue is chromatographed on 165 g
  7. customThere is obtained 4.6 g

Quellen und Nachweise

ORD-Eintrag
ord-30df19cf7fa14c4bb6861184be4a3131
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225609

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