Tetrahydrofuran → HCID 58080843, compound

HRID 1845945Notes

Reaction equation

HRID 1845945 reaction equation
[OH-].[Na+].[C:3](OC([O-])=O)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].O1CCCC1.[CH2:19]([NH:22][CH2:23][C@H:24]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37])(=[O:29])=[O:28])[CH3:25])[CH:20]=[CH2:21]>O>[CH2:19]([N:22]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:23][C@H:24]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N+:36]([O-:38])=[O:37])(=[O:29])=[O:28])[CH3:25])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 22064466Tert-butyldicarbonateHCID 66726783HCID 66726783, compound

Product 1

HCID 58080843HCID 58080843, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 2N aqueous NaOH solution (50 mL) and 6.1 g of tert-butyl dicarbonate were added to a tetrahydrofuran (100 mL) solution of 7 g of the compound obtained in Step 1, stirring at room temperature and reacted at room temperature for 6 hours. After the completion of reaction, 100 mL of water was added, followed by two extractions with 100 mL of ethyl acetate. The combined organic layer was washed with 100 mL of saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 8 g of the compound of interest as a yellow oil (86%).

Workup

  1. customreacted at room temperature for 6 hours
  2. additionwas added
  3. extractionfollowed by two extractions with 100 mL of ethyl acetate
  4. washThe combined organic layer was washed with 100 mL of saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated
  8. customthe obtained crude product
  9. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-bef94cd0580a4a4da49b57e182e88fde
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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