Sodium hydride → HCID 69085336, compound

HRID 1396289Notes

Reaction equation

HRID 1396289 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]([C:19]1[S:20][C@H:21]2[O:27][C@H:26]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:25]([OH:37])[C@H:24]([OH:38])[C@H:22]2[N:23]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([CH2:49]Br)=[CH:45][CH:44]=1>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][N:11]([C:19]1[S:20][C@H:21]2[O:27][C@H:26]([CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C@@H:25]([O:37][CH2:49][C:46]3[CH:47]=[CH:48][C:43]([O:42][CH3:41])=[CH:44][CH:45]=3)[C@H:24]([O:38][CH2:49][C:46]3[CH:47]=[CH:48][C:43]([O:42][CH3:41])=[CH:44][CH:45]=3)[C@H:22]2[N:23]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 69085606HCID 69085606, compound

Product 1

HCID 69085336HCID 69085336, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 132 (12 g, 21 mmol) in DMF (60 mL) was treated with sodium hydride (2.9 g, 84 mmol, 70% dispersed by mineral oil) for 30 minutes at 0° C., followed by addition of PMBBr (25 g, 126 mmol). After additional 1.5 hours at 15° C., the reaction was quenched with water (200 mL), and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (3×50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluted with 5%-20% ethyl acetate in petroleum ether to afford 133 as light yellow oil (8.5 g, 50%). (ES, m/z) [M+H]+ 809.0; 1H NMR (300 MHz, CDCl3) δ 7.21-7.34 (m, 9H), 6.82-6.89 (m, 4H), 6.08 (d, J=6.3 Hz, 1H), 4.52-4.57 (m, 4H), 4.50 (s, 2H), 4.33-4.35 (m, 1H), 4.05-4.06 (m, 1H), 3.84-3.91 (m, 1H), 3.81 (s, 3H), 3.80 (s, 3H), 3.58-3.66 (m, 2H), 3.31-3.54 (m, 5H), 1.56 (s, 9H), 0.96 (s, 9H), 0.14 (s, 3H), 0.07 (s, 3H).

Workup

  1. customthe reaction was quenched with water (200 mL)
  2. extractionextracted with dichloromethane (3×100 mL)
  3. washThe combined organic layer was washed with brine (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto give a residue, which
  7. customwas purified by a silica gel column
  8. washeluted with 5%-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-24be9a59ae934b229eb98c61e4402f66
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

Loading…