Methanol → HCID 66673033, compound

HRID 562609Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]butane (99.7 mg, 0.25 mmol) obtained in Example (6a) in a mixed solvent of tetrahydrofuran (0.5 ml) and methanol (0.5 ml) were added successively water (0.5 ml) and lithium hydroxide monohydrate (0.1037 g, 2.47 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 (2R)-2-amino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]butan-1-ol (74.6 mg, yield: 95%)

Workup

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

Sources & evidence

ORD record: ord-8087afd9a8d545a880c50a03a0da54c0
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067396B2

Reaction notes

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