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

HRID 903421Notes

Reaction equation

HRID 903421 reaction equation
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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 86737261Acetone sodium bicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b7964c11b5f04165a73d39ad8d1f8a19
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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