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

HRID 351864노트

반응식

HRID 351864 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-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

TFA (30 mL) was added to a solution of 5-(S)-azidomethyl-3-[4′-(tert-butoxy)carbonyl-3′-fluorophenyl]oxazolidine-2-one (6.72 g, 20 mmol) in DCM (20 mL), and the solution was kept at r.t. for 1 h. Solvents were removed under vacuum to afford 5-(S)-azidomethyl-3-(4′-carboxy-3′-fluorophenyl)oxazolidine-2-one. THF (75 mL) was added, followed by t-butanol (9.5 mL, 100 mmol), triethylamine (3.6 mL, 26 mmol), and diphenylphosphoryl azide (5.6 mL, 26 mmol). The mixture was stirred at r.t. under nitrogen atmosphere for 2 h, and then at 70° C. overnight. Solvent was removed under vacuum, and the residue distributed between ethyl acetate (150 mL) and aq. saturated sodium bicarbonate (100 mL). Aq. phase was washed with ethyl acetate (2×50 mL). Combined organic layers were washed with aq. saturated sodium bicarbonate, water, brine, and dried (MgSO4). Solvent was removed under vacuum, and the product purified by silica gel column chromatography (eluent: DCM). Yield 4.1 g (58%). MS (m/z): [M+H]+=352.

후처리

  1. customSolvents were removed under vacuum

출처 및 근거

ORD 기록
ord-8221dc7f0bfc4af083e6d9081fdcbe17
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743811B2

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