Imidazole → HCID 23519143、化合物

HRID 392816

反応式

HRID 392816 の反応式
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][C:8]([OH:10])=[O:9])[C:4](=[O:11])[O:3]1.C(O)(=O)[C@H](CC(O)=O)O.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[O:6][CH:5]([CH2:7][C:8]([O:10][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[O:9])[C:4](=[O:11])[O:3]1

参加物

7

反応物 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 222656L-Malic AcidHCID 641720(S)-2-(2,2-Dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

生成物 1

HCID 23519143HCID 23519143、化合物収率 96%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
22 °C

実験手順

A solution of (S)-(+)-2,2-dimethyl-5-oxo-1,3-dioxolane-4-acetic acid (13.20 g, 75.8 mmol), which was derived from L-malic acid by means known in the art, in N,N-dimethylformamide (25 ml) was treated at 22° C. with imidazole (10.56 g, 0.155 mmol) followed by tert-butyldimethylsilyl chloride (12.0 g, 79.6 mmol) and the resulting mixture was stirred at 22° C. for 18 h. The reaction mixture was then diluted with toluene (500 ml), washed with water (×3), saturated sodium bicarbonate and brine. After drying (magnesium sulfate), the solvent was evaporated under reduced pressure to give an oil. Distillation under vacuum gave 20.9 g (96%) of the title material as a clear oil: Bp 80-90° C./0.1 torr (bulb to bulb distillation, air bath temperature). 1H NMR (400 MHz, CDCl3) δ: 0.33 (s, 3), 0.36 (s, 3), 1.00 (s, 9), 1.11 (s, 3), 1.37 (s, 3), 2.72 (m, 2), 4.35 (dd, 1, J=4, 6).

後処理

  1. washwashed with water (×3), saturated sodium bicarbonate and brine
  2. dry with materialAfter drying (magnesium sulfate)
  3. customthe solvent was evaporated under reduced pressure
  4. customto give an oil
  5. distillationDistillation under vacuum

出典と根拠

ORDレコード
ord-085abdfc11834705b2a45f83d0e990f5
出典データセット
uspto-grants-2004_10
特許番号
US06803378B2

関連ノート

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