Hydrochloric Acid → 3-(6-Methoxy-alpha-methyl-2-naphthalenacetyl) thiazolidin-4-carboxylic acid

HRID 749220

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([OH:16])=O)[CH:7]=[CH:6]2.C(Cl)(=O)C(Cl)=O.[S:24]1[CH2:28][CH:27]([C:29]([OH:31])=[O:30])[NH:26][CH2:25]1.C(N(CC)CC)C.Cl>C1(C)C=CC=CC=1.CN(C)C=O.CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([N:26]1[CH:27]([C:29]([OH:31])=[O:30])[CH2:28][S:24][CH2:25]1)=[O:16])[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-methoxy-α-methyl-2-naphthalenacetic acid (4.02 g, 17.5 mmoles) in toluene (30 ml) and N,N-dimethylformamide (0.3 ml) cooled at 0° C., oxalylchloride (2.92 ml, 34.06 mmoles) is added. After 2 hours at room temperature, the solution is evaporated at reduced pressure. The obtained residue is dissolved in acetone (50 ml) and the solution is added to a solution of 4-thiazolidincarboxylic acid (2.33 g, 17.5 mmoles) and triethylamine (6.34 ml, 45.5 mmoles) in acetone (50 ml) cooled at 0° C. After 2 hours the solution is acidified with HCl 4 N, concentrated under vacuum, the residue is treated with ethyl acetate and the organic phase is washed first with HCl 2 N, then with water. The organic phase is anhydrified with sodium sulphate and evaporated at reduced pressure. 4.43 g of the expected product are obtained in the form of a white solid having m.p. 165° C.-168° C.

Workup

customthe solution is evaporated at reduced pressure
dissolutionThe obtained residue is dissolved in acetone (50 ml)
concentrationconcentrated under vacuum
additionthe residue is treated with ethyl acetate
washthe organic phase is washed first with HCl 2 N
customevaporated at reduced pressure

Sources & evidence

ORD record: ord-5051bfc70c824566a78e478f7ef812aa
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402600B2

Linked notes

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