Sodium hydride → HCID 58708327, compound

HRID 347331Notes

Reaction equation

HRID 347331 reaction equation
[H-].[Na+].[C:3]1([C@@H:9]([OH:24])[C@H:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>O1CCCC1>[C:30]([O:29][C:27]([CH2:26][O:24][C@H:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C@H:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 21082765HCID 21082765, compound

Product 1

HCID 58708327HCID 58708327, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% oil dispersion; 161 mg, 4.03 mmol) in dry tetrahydrofuran (9.6 ml) were added a solution of 8S (1.15 g, 3.84 mmol) and tert-butyl bromoacetate (681 μl, 4.61 mmol) in dry tetrahydrofuran (9.6 ml) at 0° C. After stirring for 18 h at rt, the reaction mixture was concentrated in vacuo. After addition of water, the product was extracted with ethyl acetate twice and the organic layer was dried over anhydrous sulfate. After concentration in vacuo, the residue was purified by silica gel chromatography (eluted with 10:1 hexane:AcOEt) to give 9S (1.17 g, 74%) as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionAfter addition of water
  3. extractionthe product was extracted with ethyl acetate twice
  4. dry with materialthe organic layer was dried over anhydrous sulfate
  5. concentrationAfter concentration in vacuo
  6. customthe residue was purified by silica gel chromatography (eluted with 10:1 hexane:AcOEt)

Sources & evidence

ORD record
ord-c236b50dd4af44c29c517383db098ff2
Source dataset
uspto-grants-2007_02
Patent number
US07173141B2

Reaction notes

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