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

HRID 749221Notes

Reaction equation

HRID 749221 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.[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

Participants

9

Reactant 4

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

Product 1

HCID 866029743-(6-methoxy-alpha-methyl-2-naphthalenacetyl)(R)-2-oxothiazolidin-4-carboxylic acidYield 68.5%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5e9a18611874429e838a1a4755b0de8f
Source dataset
uspto-grants-2008_07
Patent number
US07402600B2

Reaction notes

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