Butylamine → N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide
Reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14]C(C)(C)C)=O)[CH2:4]1.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].[Na].CC(C)([O-])C>CO>[CH2:19]([NH:23][C:12](=[O:14])[CH2:11][C@H:5]1[CH2:4][C@@H:3]([CH2:2][OH:1])[O:8][C:7]([CH3:9])([CH3:10])[O:6]1)[CH2:20][CH2:21][CH3:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 42.5 °C
Procedure
Mixture of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (100 grams), methanol (1 L), n-butyl amine (200 ml) and sodium, tertiary butoxide (74 grams) was heated to 40-45° C. and stirred up to completion of the reaction. Distilled off the reaction mixture completely under reduced pressure and water (300 ml) was added to it at 25-30° C. The reaction mixture was cooled and acidified with aqueous acetic acid. The reaction mixture washed with cyclohexane and product from aqueous layer was extracted into methylene chloride. The organic layer was washed with saturated sodium chloride solution and the solvent from it was distilled off under reduced pressure to get the title compound.
Workup
- distillationDistilled off the reaction mixture completely under reduced pressure and water (300 ml)
- additionwas added to it at 25-30° C
- temperatureThe reaction mixture was cooled
- washThe reaction mixture washed with cyclohexane and product from aqueous layer
- extractionwas extracted into methylene chloride
- washThe organic layer was washed with saturated sodium chloride solution
- distillationthe solvent from it was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-22dcbc882ac540f9b763ace2352649ca
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987444B2
Reaction notes
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