Ethylenediaminetetraacetic Acid → 3-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

HRID 913005

反応式

HRID 913005 の反応式
FC(F)C1N(C)C=C(O)C(=O)C=1.F[CH:14](F)[C:15]1[N:20](C)[C:19]([CH:22]([OH:27])[C:23]([F:26])([F:25])[F:24])=[C:18]([OH:28])[C:17](=[O:29])[CH:16]=1.C(O)C(N)(CO)CO.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>CC#N>[OH:28][C:18]1[C:17](=[O:29])[CH:16]=[C:15]([CH3:14])[NH:20][C:19]=1[CH:22]([OH:27])[C:23]([F:26])([F:24])[F:25]

参加物

6

反応物 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 6503Tris(hydroxymethyl)aminomethaneHCID 250186556-difluoromethyl-3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one2 回HCID 250189082-difluoromethyl-5-hydroxy-1-methyl-1H-pyridin-4-one2 回

生成物 1

HCID 250186523-hydroxy-6-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Proceeding in a similar manner as A, 2-difluoromethyl-5-hydroxy-1-methyl-1H-pyridin-4-one was converted to 6-difluoromethyl-3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one. 1H NMR (DMSO-d6+1 drop of D2O) δ ppm: 7.12 (t, J=52.8 Hz, 1H), 6.56 (s, 1H), 5.83 (b, 1H), 3.79 (s, 3H). 19F NMR (DMSO-d6+1 drop of D2O) δ ppm: −73.3 (3F), −117.8 (2F). MS (m/z) 274.1 [M+1]+. HPLC conditions: Column: XTerra MS C18 5 μm 4.6×250 mm. Mobile phase: A=the aqueous phase: 4 mM Tris, 2 mM EDTA, pH 7.4; B=the organic phase: CH3CN. The gradient program: B %: 0 min. 5%, 15 min. 55%, 25 min. 55%, 25.05 min. 5%, 30 min. 5%. Flow rate=1 ml/min.; injection volume=5 μL; wavelength: 220, 254, 280, 450 nm. Retention time of 2-Difluoromethyl-5-hydroxy-1-methyl-1H-pyridin-4-one=6.7 min. Retention time of 6-difluoromethyl-3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one=11.4 min.

後処理

  1. custom0 min
  2. custom5%, 15 min
  3. custom55%, 25 min
  4. custom55%, 25.05 min
  5. custom5%, 30 min

出典と根拠

ORDレコード
ord-c7c8e3f7953848709c5424ac9ec89800
出典データセット
uspto-grants-2011_09
特許番号
US08026261B2

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