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

HRID 351870노트

반응식

HRID 351870 반응식
C(O)(C(F)(F)F)=O.[N:8]([CH2:11][C@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:26]C(C)(C)C)=[O:25])=[C:20]([F:31])[CH:19]=2)[CH2:13]1)=[N+:9]=[N-:10]>C(Cl)Cl>[N:8]([CH2:11][C@H:12]1[O:16][C:15](=[O:17])[N:14]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=[O:25])=[C:20]([F:31])[CH:19]=2)[CH2:13]1)=[N+:9]=[N-:10]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 229662175-(S)-azidomethyl-3-[4'-tert-butoxycarbonyl-3'-fluorophenyl]oxazolidine-2-one

생성물 1

HCID 229662095-(S)-azidomethyl-3-(4'-carboxy-3'-fluorophenyl)oxazolidine-2-one수율 99.9%

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-2-one (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 (0.280 g, 99%). A mixture of 5-(S)-azidomethyl-3-[4′-carboxy-3′-fluorophenyl]oxazolidine-2-one well stirred mixture of (0.080 g, 0.286 mmol) and thiosemicarbazide (0.0957 g, 0.286 mmol) in dioxane (2 mL) was heated until the mixture was homogeneous. Phosphorous oxychloride (0.027 ml, 0.29 mmol) was added, and the mixture heated at reflux for 1 h. The mixture was allowed to cool to r.t., and the white precipitate filtered, washed with dioxane, suspended in saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. Combined organic extracts were washed with brine, and dried (MgSO4) Solvent was removed under vacuum, and the crude product purified by PTLC (10% MeOH in DCM) to give product as a white solid (0.038 g, 40%); MS (m/z): [M+H]+=336.

후처리

  1. customSolvents were removed in vacuo

출처 및 근거

ORD 기록
ord-dfbf92b6efd140e2925b9a84929013c5
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743811B2

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