Linezolid impurity 3 → rac-Linezolid

HRID 1166701

反応式

HRID 1166701 の反応式
C([CH2:5][C:6]([NH2:8])=[O:7])C1OC1.[C:9]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:16]([F:26])[CH:15]=1)([O:11]C)=O.[CH3:27][C:28](C)([O-:30])[CH3:29].[Li+]>C1COCC1>[F:26][C:16]1[CH:15]=[C:14]([N:13]2[CH2:27][CH:28]([CH2:29][NH:8][C:6](=[O:7])[CH3:5])[O:30][C:9]2=[O:11])[CH:19]=[CH:18][C:17]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

参加物

5

反応物 3

HCID 10944967Linezolid impurity 3HCID 222467132-OxiranepropanamideHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

生成物 1

HCID 3929rac-Linezolid収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (±)-glycidylacetamide (VIIIB, EXAMPLE 11, 0.1571 g, 1.365 mmol) in THF (1.63 ml) at −78° is added N-carbomethoxy-3-fluoro-4-morpholinylaniline (IX, PREPARATION 2, 0.4358 g, 1.71 mmol, 1.26 eq) and lithium t-butoxide (0.1267 g, 1.583 mmol, 1.16 eq). The reaction mixture is then stirred at 0 to 11° for 17.5 hrs at which point HPLC showes an 80% yield of (±)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide (retention time=0.97 min; method B; Stationary phase: 4.6×250 mm Zorbax RX C-8 column; mobile phase: 650 ml acetonitrile, 1.85 ml triethylamine, 1.30 ml acetic acid, water sufficient to make 1000 ml; flow rate: 3.0 ml/min; UV detection at 254 nm). The title compound is isolated by means known to those skilled in the art.

出典と根拠

ORDレコード
ord-ce9a10dc1eb744cf8668433f9b26cdee
出典データセット
uspto-grants-2003_09
特許番号
US06613944B2

関連ノート

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