Timonacic → 3-[4-(Hexadecylamino)cinnamoyl]-4-carboxythiazolidine

HRID 1702702Notes

Reaction equation

HRID 1702702 reaction equation
[CH2:1]([NH:17][C:18]1[CH:37]=[CH:36][C:21]([CH:22]=[CH:23][C:24]([N:26]2[CH:30]([C:31]([O:33]CC)=[O:32])[CH2:29][S:28][CH2:27]2)=[O:25])=[CH:20][CH:19]=1)[CH2:2][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][CH3:16].S1CC(C(O)=O)NC1>C(=O)(O)[O-].[Na+].CC(C)=O>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH:22]=[CH:23][C:24]([N:26]2[CH:30]([C:31]([OH:33])=[O:32])[CH2:29][S:28][CH2:27]2)=[O:25])=[CH:36][CH:37]=1)[CH2:2][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][CH3:16]

Participants

4

Reactant 2

HCID 9934TimonacicHCID 544239453-[4-(Hexadecylamino)cinnamoyl]-4-carboethoxy thiazolidine

Product 1

HCID 538485433-[4-(Hexadecylamino)cinnamoyl]-4-carboxythiazolidine

Reagents, catalysts & solvents 1

HCID 86737261Acetone sodium bicarbonateSolvent

Procedure

By means of the alkaline hydrolysis method of Example 54, the ethyl ester of Example 51 is converted to the subject carboxylic acid. This acid is also prepared using the procedure of Example 51 except that the acylation of the thiazolidine-4-carboxylic acid is carried out in aqueous acetone sodium bicarbonate solution.

Workup

  1. customBy means of the alkaline hydrolysis method of Example 54
  2. customThis acid is also prepared

Sources & evidence

ORD record
ord-3276e6d51ce04e0f984c16c2e5bea113
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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