[ClH:1].[NH2:2][C@@H:3]([CH3:10])[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[P:11](Cl)(Cl)(=[O:23])[O:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[O:12][P:11](=[N:2][C@@H:3]([CH3:10])[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5])=[O:23](S)-isopropyl 2-aminopropanoate hydrochloride (Oakwood, 500 mg, 2.98 mmol) and naphthalen-2-yl phosphorodichloridate (724 mg, 2.98 mmol) was suspended in anhydrous DCM (25 mL). The reaction was cooled to −78° C. Triethylamine (604 mg, 830 μl, 5.97 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, then allowed to warmed up to room temperature and stirred for 5 h. The solvent was removed, and the residue was washed with dry ethyl ether and filtered. The filtrate was concentrated to give crude (2S)-isopropyl 2-(chloro(naphthalen-2-yloxy)phosphorylamino)propanoate as a light yellow oil (0.8 g, 75%) and used without further purification.
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