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

HRID 351879노트

반응식

HRID 351879 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]>ClC(Cl)C>[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%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

60% TFA in dichloroethane (10 ml) was added to 5-(S)-azidomethyl-3-[4′-tert-butoxycarbonyl-3′-fluorophenyl]oxazolidine-2-one (2.00 g, 5.95 mmol; prepared as described for Example 2) and the solution kept at r.t. for 1 h. Solvent was removed under vacuum to afford 5-(S)-azidomethyl-3-[4′-carboxy-3′-fluorophenyl]oxazolidine-2-one (1.65 g, 5.89 mmol, 99%). This intermediate was dissolved in DMF (15 ml), and pentafluorophenyl trifluoroacetate (1.21 ml, 7.06 mmol) and pyridine (1.91 ml, 23.6 mmol) were added with stirring. The mixture was stirred at r.t. for 3 h, most of the solvent removed under vacuum, and the residue triturated with water. The resulting precipitate was filtered, washed with water, ether, and dried under vacuum. White crystals. Yield g (2.53 g, 93%). MS (m/z): [M+H]+=463.

후처리

  1. customSolvent was removed under vacuum

출처 및 근거

ORD 기록
ord-30a3286ca3244221a3da91c91d7e1f4d
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743811B2

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