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 75732노트

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HRID 75732 반응식
[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

참가 물질

3

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
23 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9aef7bc2cf1c4caeb9c856438f67af44
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835462B2

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