Tetrahydrofuran → HCID 86634395, compound

HRID 1191301Notes

Reaction equation

HRID 1191301 reaction equation
[Si:1]([O:18][C@H:19]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:20]1[CH2:31][OH:32])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:34][C:35](OC)=[O:36].O1CCCC1.[H-].[Na+]>O>[Si:1]([O:18][C@H:19]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:20]1[CH2:31][O:32][CH2:34][CH2:35][OH:36])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 86634393HCID 86634393, compound

Product 1

HCID 86634395HCID 86634395, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound 48 (4.56 g), methyl bromoacetate (2.22 mL) and tetrahydrofuran (25 mL) were stirred at 0° C., 60% sodium hydride suspension (400 mg) was added into the solution. The reaction solution was stirred at room temperature for overnight, added water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→85:15). The obtained compound (1.46 g) was added tetrahydrofuran (20 mL), methanol (1 mL) and lithium borohydride (117 mg) and stirred at room temperature for 2 hours. The reaction solution was added water and aqueous 5% potassium sulfate solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated and obtained the title compound (1.40 g) having the following physical properties.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→85:15)
  6. additionThe obtained compound (1.46 g) was added tetrahydrofuran (20 mL), methanol (1 mL) and lithium borohydride (117 mg)
  7. stirringstirred at room temperature for 2 hours
  8. additionThe reaction solution was added water and aqueous 5% potassium sulfate solution
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-2ab642022b6b43518a034e9b60572ce8
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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