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Methanol → HCID 58822877、化合物

HRID 459142
ノート
印刷プレビュー

反応式

HRID 459142 の反応式
C([O:3][C:4](=[O:19])[C@@H:5]([O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14]Br)=[CH:9][CH:8]=1)C.[O:20]([C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+].CO>C(#N)C.[OH-].[Na+].[Cl-].[Na+].O>[CH3:18][O:17][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[O:16])[CH2:14][O:33][C:30]2[CH:29]=[CH:28][C:27]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:32][CH:31]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 887Methanol2 回HCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 58822842HCID 58822842、化合物

生成物 1

HCID 58822877HCID 58822877、化合物

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒
HCID 14798
Sodium Hydroxide
溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

The title compound was prepared from a solution of (2S)-3-[4-(2-Bromo-acetyl)-phenyl]-2-methoxy-propionic acid ethyl ester (0.076 mmol) from Example 124, Step C in acetonitrile (5 ml). 4-phenoxyphenol (0.152 mmol) and K2CO3 (0.23 mmol) were added. The solution was stirred for 30 min at 80° C. and then cooled to room temperature. The mixture was concentrated to dryness under vacuum and chromatographed in silica gel (hexanes/Ethyl ether 8:2 to 7:3). Fractions corresponding to the coupled compound were collected (Rf: 0.27) and concentrated to dryness. The mixture thus obtained was dissolved in 4 mL of NaOH 1N and 12 mL of Methanol and stirred at room temperature until TLC indicates the disappearance of starting material. The methanol was eliminated under vacuum and the aqueous solution diluted with 20 mL of brine and washed with diethyl ether (3×15 mL). The aqueous phase was acidulated with HCl 1N (until pH 3); extracted with ethyl acetate (3×15 mL) and the organic layer dried (MgSO4) and concentrated under vacuum. Obtained a colourless oil. 1H-NMR (200.15 MHz, CDCl3): 7.96 (d, 2H, J=8.4), 7.55–7.33 (m, 5H), 7.04–6.83 (m, 6H), 5.24 (s, 2H), 4.08 (dd, 1H, J=7.4, 4.4), 3.40 (s, 3H), 3.22 (dd, 1H, J=14.3, 4.4), 3.15 (dd, 1H, J=14.3, 7.2).

後処理

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated to dryness under vacuum
  3. customchromatographed in silica gel (hexanes/Ethyl ether 8:2 to 7:3)
  4. customFractions corresponding to the coupled compound were collected (Rf: 0.27)
  5. concentrationconcentrated to dryness
  6. customThe mixture thus obtained
  7. washwashed with diethyl ether (3×15 mL)
  8. extractionextracted with ethyl acetate (3×15 mL)
  9. dry with materialthe organic layer dried (MgSO4)
  10. concentrationconcentrated under vacuum
  11. customObtained a colourless oil

出典と根拠

ORDレコード
ord-c279f7fa2e7544a29ec8a5be2f5ff2b4
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07192982B2

反応ノート

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