2-(6-Methoxy-2-naphthyl)propionic acid → 3-(6-methoxy-alpha-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acid

HRID 749221

Reaktionsgleichung

Reaktionsgleichung von HRID 749221
[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.[O:24]=[C:25]1[NH:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27][S:26]1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C)C=O.CN(C)C1C=CN=CC=1.O1CCCC1>[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:29]1[C@H:28]([C:30]([OH:32])=[O:31])[CH2:27][S:26][C:25]1=[O:24])=[O:16])[CH:7]=[CH:6]2

Komponenten

9

Edukt 4

HCID 13022-(6-Methoxy-2-naphthyl)propionic acidHCID 8471TriethylamineHCID 652722-Oxo-1,3-thiazolidine-4-carboxylic acidHCID 65578Oxalyl chloride

Produkt 1

HCID 866029743-(6-methoxy-alpha-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acidAusbeute 68,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a solution of 6-methoxy-α-methyl-2-naphthalenacetic acid (7.0 g, 30.4 mmoles) in toluene (100 ml) and N,N-dimethylformamide (10 ml) cooled at 0° C., oxalylchloride (5.23 ml, 61 mmoles) is added. After 2 hours at room temperature the solution is evaporated at reduced pressure. To the solution of the obtained residue dissolved in tetrahydrofuran (50 ml) a mixture is added consisting of 2-oxothiazolidin-4-carboxylic acid (4.07 g, 27.6 mmoles), 4-dimethylaminopyridine (0.84 g, 6.9 mmoles), triethylamine (7.69 ml, 55.2 mmoles) in tetrahydrofuran (50 ml) cooled at −10° C. The mixture is left at room temperature for 24 hours. The reaction mixture is washed with HCl 5%, then with water. The organic phase is anhydrified with sodium sulphate and then evaporated at reduced pressure. The obtained residue is purified by chromatography on silica gel eluting with methylene chloride/methanol 95/5. 6.79 g of the expected product are obtained in the form of an amorphous solid.

Aufarbeitung

  1. customAfter 2 hours at room temperature the solution is evaporated at reduced pressure
  2. dissolutionTo the solution of the obtained residue dissolved in tetrahydrofuran (50 ml) a mixture
  3. additionis added
  4. washThe reaction mixture is washed with HCl 5%
  5. customevaporated at reduced pressure
  6. customThe obtained residue is purified by chromatography on silica gel eluting with methylene chloride/methanol 95/5

Quellen und Nachweise

ORD-Eintrag
ord-5e9a18611874429e838a1a4755b0de8f
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402600B2

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