Sodium hydride → HCID 86701116, compound

HRID 1396278Notes

Reaction equation

HRID 1396278 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:16]2)[C@@H:12]([OH:28])[C@@H:11]1[OH:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+]>CN(C=O)C>[CH2:6]([O:29][C@@H:11]1[C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[O:18][C@H:17]2[C@H:13]([N:14]=[C:15]([N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[S:16]2)[C@H:12]1[O:28][CH2:11][CH:10]=[CH2:9])[CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 69280761HCID 69280761, compound

Product 1

HCID 86701116HCID 86701116, compoundYield 155.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

A solution of 26 (35 g, 78 mmol) (Prepared according to the synthesis of Example 3, step 4) in DMF (250 mL) was treated with NaH (70%, 8 g, 233 mmol) at 5° C. for 30 min, then Allyl-Br (28 g, 233 mmol) was added slowly. After stirring for 1.5 hours at 15° C., the reaction was quenched by H2O (300 mL), extracted with ethyl acetate (3×200 mL). The organic layers were collected, washed with brine (5×100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue, which was purified by a silica gel column, eluted with 5%˜10% ethyl acetate in petroleum ether to afford the title compound (32 g, 78%) as a yellow oil; (ES, m/z) [M+H]+ 529.1; 1H NMR (300 MHz, CDCl3) δ 6.07 (d, J=6.3 Hz, 1H), 5.85-6.05 (m, 2H), 5.15-5.38 (m, 4H), 4.22-4.30 (m, 4H), 4.02-4.07 (m, 2H), 3.76-3.78 (m, 2H), 3.60-3.62 (m, 1H), 3.48-3.52 (m, 1H), 3.31 (s, 3H), 1.55 (s, 9H), 0.93 (s, 9H), 0.08 (s, 6H).

Workup

  1. customthe reaction was quenched by H2O (300 mL)
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. customThe organic layers were collected
  4. washwashed with brine (5×100 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue, which
  8. customwas purified by a silica gel column
  9. washeluted with 5%˜10% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-2edb2dbe6b874c3192c5ea81aed7cdad
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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