Trifluoroacetic acid → 5-(S)-azidomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazolidine-2-one

HRID 351857노트

반응식

HRID 351857 반응식
C(O)(C(F)(F)F)=[O:2].[N:8]([CH2:11][C@H:12]1[O:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25]C(C)(C)C)=[O:24])=[C:19]([F:30])[CH:18]=2)[CH2:13]1)=[N+:9]=[N-:10]>C(Cl)Cl>[N:8]([CH2:11][C@H:12]1[O:16][C:15](=[O:2])[N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[C:19]([F:30])[CH:18]=2)[CH2:13]1)=[N+:9]=[N-:10]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 207299935-(s)-Azidomethyl-3-[4'-tert-butoxycarbonyl-3'-fluorophenyl]oxazolidine

생성물 1

HCID 229662095-(S)-azidomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazolidine-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

60% TFA in DCM (5 mL) was added to 5-(S)-azidomethyl-3-[4′-tert-butoxycarbonyl-3′-fluorophenyl]oxazolidine (0.336 g, 1 mmol), and the solution kept at r.t. for 1 h. Solvents were removed in vacuo to afford 5-(S)-azidomethyl-3-[4′-carboxy-3′-fluorophenyl-]oxazolidine-2-one dried (0.280 g, 99%). N-Trimethylsilyl-N,N-diethylamine (0.23 mL, 1.2 mmol) was added to above product in dry dichloromethane (3 mL) under nitrogen atmosphere, and the solution stirred for 15 min. Solvents and excess reagent were removed in vacuo, and residue dissolved in dichloromethane (4 mL). The solution was cooled to about 0° C., and oxalyl chloride (1.5 mmol, 0.13 mL) was added dropwise, followed by catalytic N,N-dimethylformamide (about 0.01 mL). The mixture was allowed to warm up to r.t. (room temperature), and stirred at r.t. for another 2 h. Solvents were removed in vacuo to afford the product as a white solid. Yield 0.292 g (98%).

후처리

  1. customSolvents were removed in vacuo

출처 및 근거

ORD 기록
ord-6e977c823bdb4a9b9c2540ec311b1773
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743811B2

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