N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide → (3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one

HRID 75732ノート

反応式

HRID 75732 の反応式
[CH2:1]([C@@H:8]1[C@@H:16]([OH:17])[C@H:15]([CH3:18])[O:14][C:13](=[O:19])[C@@H](NC(=O)C2C(O)=C(OC)C=CN=2)COC1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>Cl>[CH2:1]([C@@H:8]1[C@@H:16]([OH:17])[C@H:15]([CH3:18])[O:14][C:13]1=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 11236123N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

生成物 1

HCID 10608337(3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one収率 70%

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
23 °C

実験手順

A suspension of N-((3S,7R,8R,9S)-7-benzyl-8-hydroxy-9-methyl-2,6-dioxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide, prepared as described by Ricks, Michael J. et al. in U.S. Pat. No. 6,706,740 2004, (20.0 grams (g), 38.7 millimole (mmol), 1.00 equivalent (equiv)) in 6M HCl (200 milliliters (mL)) was heated to 100° C. with rapid stirring. After 1 hour (h), the resulting brown solution was cooled to 23° C. and extracted with diethyl ether (Et2O; 2×200 mL). The organic extracts were combined, washed with saturated (sat'd) aqueous sodium bicarbonate (NaHCO3) solution (100 mL), dried over magnesium sulfate (MgSO4), filtered, and concentrated to provide (3R,4R,5S)-3-benzyl-4-hydroxy-5-methyldihydrofuran-2(3H)-one (5.62 g, 70%) as a tan solid.

後処理

  1. customprepared
  2. extractionextracted with diethyl ether (Et2O; 2×200 mL)
  3. washwashed with saturated (sat'd) aqueous sodium bicarbonate (NaHCO3) solution (100 mL)
  4. dry with materialdried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9aef7bc2cf1c4caeb9c856438f67af44
出典データセット
uspto-grants-2014_09
特許番号
US08835462B2

反応ノート

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