Reaction SMILES: [CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:37])[C@@H:15]([CH2:35][CH3:36])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:33][CH3:34])=[C:21]([CH:32]=1)[C:22]([O:24]CC1C=CC=CC=1)=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:37])[C@@H:15]([CH2:35][CH3:36])[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:33][CH3:34])=[C:21]([CH:32]=1)[C:22]([OH:24])=[O:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
Reactant: CC[C@@H](Cc1ccc(OC)c(C(=O)OCc2ccccc2)c1)C(=O)N1C(=O)OC[C@H]1Cc1ccccc1
Agent: [Pd]
Solvent: CCOC(C)=O
Product: CC[C@@H](Cc1ccc(OC)c(C(=O)O)c1)C(=O)N1C(=O)OC[C@H]1Cc1ccccc1
Temperature: 35 °C
Reaction time: 5 h

Procedure:
To a solution of 104 g (0.207 mol) of benzyl 5-[3-[4-(R)-benzyl-2-oxo-1,3-oxazolidine-3-yl]-2-(S)-ethyl-3-oxopropyl]-2-methoxybenzoate (Jpn. Kokai Tokkyo Koho JP 2001-55367 (Example 165)) in 728 ml of ethyl acetate (AcOEt) were added 6.93 g of 10% palladium on carbon (Pd—C) (dry article), and the mixture was stirred for 5 hours at inner temperature of 35° C. under an atmosphere of hydrogen. After the catalyst was filtered off, the reaction mixture was concentrated under reduced pressure to obtain colorless oily 5-[3-[4-(R)-benzyl-2-oxo-1,3-oxazolidine-3-yl]-2-(S)-ethyl-3-oxopropyl]-2-methoxybenzoic acid. This oily product was dissolved into 413 mL of dehydrated dimethylformamide (DMF) and, after 62.9 g (0.622 mol) of triethylamine (Et3N) were added, the mixture was stirred under cooling with ice water. At inner temperature of 5° C., 22.5 g (0.207 mol) of ethyl chloroformate were added dropwise (inner temperature increased to 8° C.) and thereafter the mixture was stirred for 1 hour. Then, 55.2 g (0.218 mol) of [4-(4-fluorophenoxy)phenyl]methylamine hydrochloride were put in at inner temperature of 6° C. and the mixture was stirred for 1 hour. The reaction mixture was poured into 826 mL of water, which was extracted twice (516 mL, 309 mL) with ethyl acetate. The ethyl acetate layers were combined, washed with 207 mL of 1 mol/L aqueous solution of sodium hydroxide (NaOH aq.), 405 mL of water and 36 mL of saturated brine in sequence, then dried over anhydrous sodium sulfate, and solvent was distilled off under reduced pressure. The product was dried (vacuum pump) for 2 hours at room temperature under reduced pressure to obtain 126 g of pale yellow oily N-[4-(4-fluorophenoxy)phenyl]methyl-5-[3-[4-(R)-benzyl-2-oxo-1,3-oxazolidine-3-yl]-2-(S)-ethyl-3-oxopropyl]-2-methoxybenzamide. This oily product was dissolved into 806 mL of tetrahydrofuran (THF) and, after 202 mL of purified water were added, the mixture was stirred under cooling with ice water. To this solution were added dropwise 91 mL (0.829 mol) of 31% aqueous hydrogen peroxide (H2O2) over 10 minutes at inner temperature of 8° C. Following this, a solution of 13.9 g (0.332 mol) of lithium hydroxide monohydrate (LiOH.H2O) in 556 mL of purified water were added dropwise over 80 minutes at inner temperature of 8 to 10° C. and the mixture was stirred further for 1 hour. After a solution of 86.2 g of sodium hydrogensulfite (NaHSO3) in 432 mL of purified water were added dropwise over 20 minutes, the mixture was stirred for 1 hour. After allowed to stand statically, the aqueous layer was separated, which was extracted with 259 mL of ethyl acetate pH value of aqueous layer 1.33: pH meter). The organic layers were combined and solvent was distilled off under reduced pressure. The residue was dissolved into 518 mL of ethyl acetate and, after washing with 415 mL of cold water, the solution was extracted twice with cold aqueous solution of alkali prepared with 570 mL of ice water and 570 mL of 1 mol/L NaOH aq. The aqueous layers were combined and 273 mL of 6 mol/L hydrochloric acid (HCl aq.) were added, which was then extracted with 829 mL and 311 mL of ethyl acetate. The ethyl acetate layers were combined, washed with 270 mL of saturated aqueous solution of sodium hydrogencarbonate (pH value of washed liquid: 7.38, pH meter) and 41 mL of saturated brine in sequence, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the residue were added 207 mL of ethyl acetate and 21 mL of isopropyl alcohol (IPA). After dissolved by heating, 311 mL of hexane were added. The mixture was stirred at room temperature under cooling by allowing to stand and stirred at inner temperature of 30° C. under cooling with ice water. After stirring for 1 hour at inner temperature of below 10° C., the precipitated crystals were collected by filtration at inner temperature of 6° C. After washing with 173 mL of mixed solution of hexane/ethyl acetate (3:1), the crystals were dried for 3 hours at 50° C. by blower to obtain 75.0 g of crude crystals of compound (I). After dissolved 75.0 g of crude crystals into 483 mL of ethanol (EtOH) by heating, 257 mL of purified water were added. After stirring under cooling with water, the solution was cooled with ice water at inner temperature of 25° C. and stirred for 1 hour at inner temperature of below 10° C. The precipitated crystals were collected by filtration at inner temperature of 4° C. and, after washing with 357 mL of 25% EtOH/water, the crystals were dried for 1 hour by blower. These were dried at 50° C. until they became constant weight to obtain 73.3 g (yield 78%) of the compound of the present application.