Chloroform → 3-[4-(8-Cyclohexyloctylamino)benzoyl]carboxythiazolidine

HRID 903421

Reaktionsgleichung

Reaktionsgleichung von HRID 903421
Cl.[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[S:26]1[CH2:30][CH:29](C(OCC)=O)[NH:28][CH2:27]1.C(Cl)(Cl)Cl.S1CC([C:45]([OH:47])=[O:46])NC1>C(Cl)Cl.C(=O)(O)[O-].[Na+].CC(C)=O.C(N(CC)CC)C>[CH:2]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([N:28]3[CH2:29][CH2:30][S:26][CH:27]3[C:45]([OH:47])=[O:46])=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 9934TimonacicHCID 103574Ethyl thiazolidine-4-carboxylateHCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

Produkt 1

HCID 204758133-[4-(8-Cyclohexyloctylamino)benzoyl]carboxythiazolidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 86737261Acetone sodium bicarbonateLösungsmittel

Versuchsvorschrift

One-tenth mole of 4-(8-cyclohexyloctylamino)benzoyl chloride hydrochloride in methylene chloride is added to a solution of 0.1 mole of ethyl thiazolidine-4-carboxylate in chloroform containing two equivalents of triethylamine. After 5 hours at 20° C. the solution is filtered and evaporated to a white solid which is recrystallized from acetonitrile. By means of the alkaline hydrolysis method of Example 1, the ethyl ester is converted to the subject carboxylic acid. This acid is also prepared using the procedure of this Example except that the acylation of the thiazolidine-4-carboxylic acid is carried out in aqueous acetone sodium bicarbonate solution.

Aufarbeitung

  1. filtrationAfter 5 hours at 20° C. the solution is filtered
  2. customevaporated to a white solid which
  3. customis recrystallized from acetonitrile
  4. customBy means of the alkaline hydrolysis method of Example 1
  5. customThis acid is also prepared

Quellen und Nachweise

ORD-Eintrag
ord-b7964c11b5f04165a73d39ad8d1f8a19
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04227014

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