Methanol → HCID 24967249, compound

HRID 1803835Notes

Reaction equation

HRID 1803835 reaction equation
C([C@H:4]1[C@@H:21]([OH:22])[CH2:20][CH2:19][C@@:18]2([CH3:23])[C:5]1=[CH:6][CH2:7][C@@H:8]1[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]1[CH2:10][C@@H:11]([OH:25])[C@@H:12]2[OH:24])(=O)C.C[OH:27]>[OH-].[Na+]>[CH3:14][C@:13]12[CH2:15][CH2:16][C@H:17]3[C@@H:8]([CH2:7][CH:6]=[C:5]4[C@:18]3([CH3:23])[CH2:19][CH2:20][C@H:21]([OH:22])[C@@H:4]4[OH:27])[C@@H:9]1[CH2:10][C@@H:11]([OH:25])[C@@H:12]2[OH:24]

Participants

4

Reactant 2

HCID 887MethanolHCID 69046303HCID 69046303, compound

Product 1

HCID 24967249HCID 24967249, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The compound 7 (50 mg, 0.137 mmol) was dissolved in 1 N sodium hydroxide aqueous (1 mL) and methanol (5 mL) and the resulting solution was refluxed for 1 hr. Methanol was removed under vacuum and the residue was extract with ethyl acetate (3×30 mL). The combined extracts were dried over magnesium sulfate, filtered, and concentrated under vacuum to afford a solid. The crude product was purified by recrystallization from methanol to afford title compound 8 ((23 mg) as a white solid. Selected 1H NMR data: (CD3OD, 300 MHz): δ 5.62 (d, 1H, J=3.2 Hz), 4.05 (d, 1H, J=2.4 Hz), 4.02 (m, 1H), 3.43 (dt, br, 1H, J=11.7 Hz, 3.6 Hz), 3.36 (d, 1H, J=4.2 Hz), 1.197 (s, 3H), 0.76 (s, 3H). Melting Point: 238-241° C.

Workup

  1. customMethanol was removed under vacuum
  2. extractionthe residue was extract with ethyl acetate (3×30 mL)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto afford a solid
  7. customThe crude product was purified by recrystallization from methanol

Sources & evidence

ORD record
ord-c7b980bb4a4949e0b4464d9c2a9c9ce0
Source dataset
uspto-grants-2013_01
Patent number
US08354396B2

Reaction notes

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