Benzyl Bromide → HCID 67281599、化合物

HRID 913023ノート

反応式

HRID 913023 の反応式
[OH-].[Na+].[OH:3][C:4]1[C:9](=[O:10])[CH:8]=[C:7]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])[N:6]([CH3:17])[C:5]=1[CH2:18][OH:19].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[CH2:20]([O:3][C:4]1[C:9](=[O:10])[CH:8]=[C:7]([CH:11]([OH:16])[C:12]([F:15])([F:13])[F:14])[N:6]([CH3:17])[C:5]=1[CH2:18][OH:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 67282310HCID 67282310、化合物

生成物 1

HCID 67281599HCID 67281599、化合物収率 76%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A 6.00 N sodium hydroxide solution (785 μL, 4.71 mmol) was added to a suspension of 3-hydroxy-2-hydroxymethyl-1-methyl-6-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (1.08 g, 4.26 mmol) in methanol (5 mL). Benzyl bromide (650 μL, 5.46 mmol) was added to the clear solution, and the resulting solution was heated to reflux for 45 min Some solid had separated out in the solution. Analysis of the reaction mixture using HPLC Method 1 (Example 24) indicated that the starting material was consumed. The reaction mixture was allowed to cool down to room temperature, and the first crop of solid product was collected by suction filtration, and washed with acetonitrile. The title compound was thus obtained as a solid product (1.11 g, 76% yield, HPLC Method 1 (Example 24), RT=12.6 min, HPLC purity (peak percent area): 99% at x=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 7.36 (m, 5H), 6.59 (s, 1H), 5.53 (q, J=6.5 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 3.72 (s, 3H).

後処理

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 45 min Some solid
  3. customhad separated out in the solution
  4. customwas consumed
  5. filtrationthe first crop of solid product was collected by suction filtration
  6. washwashed with acetonitrile

出典と根拠

ORDレコード
ord-76830375dfba4d2ebe4fbbc55b73f2fd
出典データセット
uspto-grants-2011_09
特許番号
US08026261B2

反応ノート

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