反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[NH2:5].[CH2:15]([NH:22][C:23](=[O:25])[O-])[C:16]1C=CC=C[CH:17]=1.Cl[C:27]([O:29]CC1C=CC=CC=1)=[O:28].[CH2:37]([Li])CCC.C(N)(=O)C>C(=O)(O)[O-].[Na+]>[CH3:37][C:23]([NH:22][CH2:15][C@@H:16]1[O:29][C:27](=[O:28])[N:5]([C:4]2[CH:6]=[CH:7][C:8]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[C:2]([F:1])[CH:3]=2)[CH2:17]1)=[O:25]参加物
実験手順
Fluorination of 4-chloronitrobenzene with fluorine gas in sulfuric acid provided 4-chloro-3-fluoronitrobenzene as a crystalline solid on aqueous workup of the reaction. This was followed by displacement of the chloro group with morpholine (neat) in quantative yield, isolated as a crystalline solid on dilution of the reaction with methanol. Reduction of the nitro group with ammonium formate under an argon or nitrogen atmosphere provided 3-fluoro-4-morpholinoaniline as a crystalline solid which was converted to the isocyanate and treated with the chiral epoxide (S)N-(oxiranylmethyl)acetamide in xylene with lithium bromide and tributylphosphine oxide to yield linezolid. Alternatively, the intermediate 3-fluoro-4-morpholinoaniline was converted to the benzylcarbamate with benzyl chloroformate in aq. sodium bicarbonate, and subsequently treated with n-butyl lithium to form the anion and treated with (S)N-oxiranylmethyl)acetamide to provide linezolid.
後処理
- customto form the anion
出典と根拠
- ORDレコード
- ord-f2a30be05fab400fbe9a38e4006650b6
- 出典データセット
- uspto-grants-2015_12
- 特許番号
- US09206141B2
関連ノート
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