Methanol → HCID 66673192, compound

HRID 422912Notes

Reaction equation

HRID 422912 reaction equation
[C:1]([O:4][CH2:5][C@@:6]([NH:27]C(=O)C)([CH2:25][CH3:26])[CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14]#[C:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:13]=1)(=[O:3])[CH3:2].O1CCCC1.CO.[OH2:38].[OH-:39].[Li+]>O>[C:2]([OH:39])(=[O:38])[C:1]([OH:4])=[O:3].[NH2:27][C@:6]([CH2:25][CH3:26])([CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14]#[C:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)=[CH:12][CH:13]=1)[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66672502HCID 66672502, compound

Product 1

HCID 66673192HCID 66673192, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of (2R)-1-acetoxy-2-acetylamino-2-ethyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butane obtained in Example (25a) in a mixed solvent of tetrahydrofuran (0.5 ml), methanol (0.5 ml) and water (0.5 ml) was added lithium hydroxide monohydrate (44.7 mg, 1.07 mmol) with stirring, and the resulting mixture was stirred at 50° C. for 4 hours. After cooling, water was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a basic silica gel column (NH type) using a mixed solvent of dichloromethane and methanol (1:0-50:1) as the eluent to afford the crude (2R)-2-amino-2-ethyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butan-1-ol (35.3 mg, yield: 99%).

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 4 hours
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by chromatography on a basic silica gel column (NH type)

Sources & evidence

ORD record
ord-1b70894cd1104a6b8f6f52f597909643
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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