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Methanol → HCID 58822877, 화합물

HRID 459142
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HRID 459142 반응식
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]
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참가 물질

8

반응물 4

HCID 887Methanol2회HCID 11430Potassium CarbonateHCID 132544-PhenoxyphenolHCID 58822842HCID 58822842, 화합물

생성물 1

HCID 58822877HCID 58822877, 화합물

시약·촉매·용매 3

HCID 6342Acetonitrile용매
HCID 14798
Sodium Hydroxide
용매
HCID 57417360Sodium chloride; water용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c279f7fa2e7544a29ec8a5be2f5ff2b4
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07192982B2

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