Methanol → HCID 66672905, compound

HRID 422909Notes

Reaction equation

HRID 422909 reaction equation
C([O:4][CH2:5][C@@:6]([NH:27]C(=O)C)([CH3:26])[CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14](=[O:25])[CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1)(=O)C.O1CCCC1.CO.[OH2:38].[OH-:39].[Li+]>O>[C:17]([OH:18])(=[O:39])/[CH:16]=[CH:15]/[C:14]([OH:25])=[O:38].[NH2:27][C@:6]([CH3:26])([CH2:7][CH2:8][C:9]1[O:10][C:11]([C:14](=[O:25])[CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1)[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66672877HCID 66672877, compound

Product 1

HCID 66672905HCID 66672905, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-[5-(4-phenyloxybutanoyl)furan-2-yl]butane (0.2031 g, 0.49 mmol) obtained in Example (21a) in a mixed solvent of tetrahydrofuran (1.0 ml) and methanol (1.0 ml) were added successively water (1.0 ml) and lithium hydroxide monohydrate (0.2065 g, 4.92 mmol), 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 (100:1) as the eluent to afford the crude (2R)-2-amino-2-methyl-4-[5-(4-phenyloxybutanoyl)furan-2-yl]butan-1-ol (58.4 mg).

Workup

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

Sources & evidence

ORD record
ord-76edec192a36405ea73c7620f34678ca
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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