Chloroform → 3-[4-(16-Bromohexadecylamino)benzoyl]-4-carboxythiazolidine

HRID 648322Notes

Reaction equation

HRID 648322 reaction equation
Cl.[Br:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.[S:29]1[CH2:33][CH:32]([C:34]([O:36]CC)=[O:35])[NH:31][CH2:30]1.C(Cl)(Cl)Cl.C(N(CC)CC)C>C(Cl)Cl>[Br:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:31]2[CH:32]([C:34]([OH:36])=[O:35])[CH2:33][S:29][CH2:30]2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 103574Ethyl thiazolidine-4-carboxylateHCID 130254084-(16-Bromohexadecylamino)benzoyl chloride hydrochloride

Product 1

HCID 130254103-[4-(16-Bromohexadecylamino)benzoyl]-4-carboxythiazolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One-tenth mole of 4-(16-bromohexadecylamino)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 to yield 3-[4-(16-bromohexadecylamino)benzoyl]-4-carboxythiazolidine. By means of the alkaline hydrolysis method of Example 10, 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

Sources & evidence

ORD record
ord-f2cb39de5bb44b23ac25513cebce2033
Source dataset
uspto-grants-1983_10
Patent number
US04411903

Reaction notes

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