Hydrazine hydrate (1:1) → tert-butyl(2S,3S)-2-[(2-aminoethyl)amino]-3-methylpentanoate
Reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][NH:14][C@@H:15]([C@@H:23]([CH3:26])[CH2:24][CH3:25])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O.NN>C(O)C.[OH-].[Na+].O>[NH2:3][CH2:12][CH2:13][NH:14][C@@H:15]([C@@H:23]([CH3:26])[CH2:24][CH3:25])[C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
To a solution of Example 32B (12.9 g) in ethanol (400 mL) was added hydrazine hydrate (11.2 mL). The solution was then heated to 70° C. for 2 hrs. After cooling to 25° C., the resulting solid was dissolved in 1N NaOH solution (200 mL) and water (200 mL). The solution was then extracted with dichloromethane (3×200 mL), the organic extracts combined, dried and evaporated to provide 6.8 g of the title compound.
Workup
- temperatureAfter cooling to 25° C.
- extractionThe solution was then extracted with dichloromethane (3×200 mL)
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-117501ef810c4ec681e9e8f191508dbd
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653141B2
Reaction notes
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