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

HRID 2163771

Reaction equation

HRID 2163771 reaction equation
[CH2:1]([NH:17][C:18]1[CH:35]=[CH:34][C:21]([C:22]([N:24]2[CH:28]([C:29]([O:31]CC)=[O:30])[CH2:27][S:26][CH2:25]2)=[O:23])=[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]([C:22]([N:24]2[CH:28]([C:29]([OH:31])=[O:30])[CH2:27][S:26][CH2:25]2)=[O:23])=[CH:34][CH:35]=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 204373423-[4-(Hexadecylamino)benzoyl]-4-carboethoxythiazolidine

Product 1

HCID 204373653-[4-(Hexadecylamino)benzoyl]-4-carboxythiazolidine

Reagents, catalysts & solvents 1

HCID 86737261Acetone sodium bicarbonateSolvent

Procedure

By means of the alkaline hydrolysis method of Example 7, the ethyl ester of Example 21 is converted to the subject carboxylic acid. This acid is also prepared using the procedure of Example 21 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 7
  2. customThis acid is also prepared

Sources & evidence

ORD record
ord-5b11191574bb446b90494df4117a7bc3
Source dataset
uspto-grants-1979_01
Patent number
US04136256

Linked notes

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