Hydrochloric Acid → [5-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-3-methyl-pent-3-enyl]-phosphonic acid monoethyl ester

HRID 272125

反応式

HRID 272125 の反応式
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][C:11]([CH3:28])=[CH:12][CH2:13][C:14]1[C:15]([OH:27])=[C:16]2[C:20](=[C:21]([CH3:25])[C:22]=1[O:23][CH3:24])[CH2:19][O:18][C:17]2=[O:26])(=[O:8])[O:5]CC)[CH3:2].[Li+].[OH-].CO.Cl>[Cl-].[Na+].O.O>[CH2:1]([O:3][P:4]([CH2:9][CH2:10][C:11]([CH3:28])=[CH:12][CH2:13][C:14]1[C:15]([OH:27])=[C:16]2[C:20](=[C:21]([CH3:25])[C:22]=1[O:23][CH3:24])[CH2:19][O:18][C:17]2=[O:26])(=[O:5])[OH:8])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 76548183[5-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-3-methyl-pent-3-enyl]-phosphonic acid diethyl ester

生成物 1

HCID 76548828[5-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-3-methyl-pent-3-enyl]-phosphonic acid monoethyl ester収率 28%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
70 °C

実験手順

A mixture of [5-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-3-methyl-pent-3-enyl]-phosphonic acid diethyl ester (27 mg, 0.066 mmol), LiOH (200 mg), MeOH (3 mL) and water (1 mL) was stirred at 70° C. for 4 h. After cooling, the reaction solution was acidified with 2 N HCl, mixed with brine, and extracted with ethyl acetate/acetonitrle. The organic extract was concentrated and the residue was purified by preparative reverse-phase HPLC (acetonitrile and 0.1% aqueous CF3COOH), affording [5-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-3-methyl-pent-3-enyl]-phosphonic acid monoethyl ester (7 mg, 28%); 1H NMR (300 MHz, CD3OD) δ 1.28 (t, J=6.9, 3H), 1.7-1.9 (m, 5H), 2.20 (s, 3H), 2.2-2.3 (m, 2H), 3.41 (d, J=6.6 Hz, 2H), 3.80 (s, 3H), 4.02 (m, 2H), 5.2-5.3 (m, 3H).

後処理

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate/acetonitrle
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. customthe residue was purified by preparative reverse-phase HPLC (acetonitrile and 0.1% aqueous CF3COOH)

出典と根拠

ORDレコード
ord-cc98f93d57a740bca805aa8d3c5cde6c
出典データセット
uspto-grants-2008_11
特許番号
US07452901B2

関連ノート

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