Water → (2R)-2-Allyloxycarbonylamino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl) furan-2-yl]butan-1-ol
Reaction equation
Cl.[NH2:2][C@:3]([CH3:24])([CH2:6][CH2:7][C:8]1[O:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:11][CH:12]=1)[CH2:4][OH:5].O.C(=O)([O-])O.[K+].Cl[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33]>C(OCC)(=O)C>[CH2:35]([O:34][C:32]([NH:2][C@:3]([CH3:24])([CH2:6][CH2:7][C:8]1[O:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[CH:11][CH:12]=1)[CH2:4][OH:5])=[O:33])[CH:36]=[CH2:37]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of (2R)-2-amino-2-methyl-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]butan-1-ol (0.5305 g, 1.66 mmol) obtained in Example 20 in a mixed solvent of ethyl acetate (16 ml) and water (16 ml) were added potassium hydrogencarbonate (0.1995 g, 1.99 mmol) first and then allyl chloroformate (0.21 ml, 1.98 mmol) with stirring, and the resulting mixture was stirred at room temperature for 30 minutes. After stirring, the reaction mixture was diluted with ethyl acetate and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo to afford the title compound (0.6202 g, yield: 93%)
Workup
- stirringAfter stirring
- extractionextracted with ethyl acetate
- 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
Sources & evidence
- ORD record
- ord-629682c130f742f09c0c2a8c8303c03f
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199150B2
Reaction notes
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