Reaction SMILES: [O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](Cl)=[O:10].[CH3:15][O:16][C:17](=[O:27])[C:18]1[CH:26]=[CH:25][CH:24]=[C:20]([C:21]([OH:23])=O)[CH:19]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:50][O:51][CH:52]([O:55][CH3:56])[CH2:53][NH2:54]>CN(C=O)C.O>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([C:9](=[O:10])[CH2:18][C:17]([OH:27])=[O:16])[CH:12]=[CH:13][CH:14]=1.[CH3:15][O:16][C:17](=[O:27])[C:18]1[CH:26]=[CH:25][CH:24]=[C:20]([C:21]([NH:54][CH2:53][CH:52]([O:55][CH3:56])[O:51][CH3:50])=[O:23])[CH:19]=1
Reactant: O=C(Cl)c1cccc(-c2ncco2)c1
Reactant: COC(CN)OC
Reactant: COC(=O)c1cccc(C(=O)O)c1
Agent: CCN=C=NCCCN(C)C
Agent: Cl
Agent: On1nnc2ccccc21
Solvent: CN(C)C=O
Solvent: O
Product: COC(=O)c1cccc(C(=O)NCC(OC)OC)c1
Product: O=C(O)CC(=O)c1cccc(-c2ncco2)c1
Temperature: 0 °C

Procedure:
The 3-(3-oxazol-2-yl-phenyl)-3-oxo-propionic acid was prepared from 3-oxazol-2-yl-benzoyl chloride [prepared by the following sequence: i.) To a solution of isophthalic acid monomethyl ester (5.83 g) in DMF (150 mL) were added at −35° C. 88% 1-hydroxy-benzotriazole (7.83 g) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (9.78 g) and the mixture was stirred for 10 min. A solution of amino-acetaldehyde dimethylacetal (4.53 mL) in DMF (30 mL) was added dropwise over 10 min. The mixture was allowed to warm up to 0° C. over 2 h, diluted with H2O and extracted with EtOAc. The organic layer was washed successively with 5% aqueous citric acid, sat. NaHCO3-solution and brine, dried over Na2SO4 and evaporated in vacuum to give 3-[N-(2,2-dimethoxy-ethyl)-aminocarbonyl]-benzoic acid methyl ester (8.2 g) as an oil. ii.) To a solution of this material (5.4 g) in THF (40 mL) was added 6N HCl (10 mL). After being stirred 20° C. for 2 h, the mixture was partitioned between EtOAc and brine. The organic layer was dried and evaporated to give 3-[N-(2-oxo-ethyl)-aminocarbonyl]-benzoic acid methyl ester (4.0 g) as an oil. iii.) A solution of this material (4.0 g) in dichloromethane (35 mL) was added at 20° C. to a solution of iodine (9.1 g) and triphenylphosphine (9.4 g) in dichloromethane (350 mL). The brown solution was stirred at 20° C. for 0.5 h and subsequently washed with 0.1M sodium thiosulfate solution and H2O, dried over Na2SO4 and evaporated to give 3-oxazol-2-yl-benzoic acid methyl ester (1.05 g) as light-brown solid, mp. 64-70° C. iv.) A mixture of this material (0.41 g), EtOH (4 mL) and 2N KOH (2 mL) was heated to 80° C. for 1.5 h. The solution was diluted with H2O and washed with diethylether. The aqueous layer was acidified with 3N HCl and the product was extracted with EtOAc to give 3-oxazol-2-yl-benzoic acid (0.28 g) as a light-brown solid, mp. 187-188° C. v.) This carboxylic acid (4.2 g) was heated with thionyl chloride in toluene and the resulting carboxylic acid chloride was used directly in the next step.] (4.4 g) and bis(trimethylsilyl)malonate with n-BuLi in ether at −60° C. to 0° C. according to general procedure K (method c2). The crude material was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure L (method a). Obtained as pale-yellow crystals (1.8 g).