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

HRID 351857ノート

反応式

HRID 351857 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  1. customSolvents were removed in vacuo

出典と根拠

ORDレコード
ord-6e977c823bdb4a9b9c2540ec311b1773
出典データセット
uspto-grants-2004_06
特許番号
US06743811B2

反応ノート

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