Tetrahydrofuran → HCID 67490909, compound

HRID 1917374Notes

Reaction equation

HRID 1917374 reaction equation
[OH-].[Na+].O1CCCC1.C[O:9][C:10]([C@@:12]12[CH2:20][N:19]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:18][C@@H:17]1[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11]>CO>[CH2:24]([O:23][C:21]([N:19]1[CH2:20][C@:12]2([C:10]([OH:11])=[O:9])[C@@H:17]([CH2:16][CH2:15][CH2:14][CH2:13]2)[CH2:18]1)=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67490844HCID 67490844, compound

Product 1

HCID 67490909HCID 67490909, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 mol/L sodium hydroxide solution (70.8 mL) and tetrahydrofuran (78.8 mL) were added to a solution of [(1R*,6R*)-8-benzyloxycarbonyl-8-azabicyclo[4.3.0]nonan-1-yl]carboxylic acid methyl ester (7.50 g, 23.6 mmol) in methanol (78.8 mL) in a nitrogen atmosphere, and the mixture was stirred at room temperature for three days. The reaction solution was concentrated under reduced pressure and then washed with diethyl ether (50 mL×2). The aqueous layer was made acidic with 3 mol/L hydrochloric acid (28 mL) under ice-cooling, followed by extraction with ethyl acetate (100 mL×2). The organic layer was washed with brine (250 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 6.70 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. washwashed with diethyl ether (50 mL×2)
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate (100 mL×2)
  5. washThe organic layer was washed with brine (250 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac30b4ed186f4077a12cd536b0d7f8ca
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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