Methanol → Methyl 2-amino-4,4-dimethylpentanoate
Reaction equation
[NH2:1][CH:2]([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].S(Cl)(Cl)=O.[CH3:15]O>>[CH3:15][O:4][C:3](=[O:5])[CH:2]([NH2:1])[CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8]Participants
4
Procedure
2-Amino-4,4-dimethyl-pentanoic acid (1.00 g, 6.84 mmol) was suspended in 50 mL of methanol and cooled in an ice bath. Thionyl chloride (1.82 g, 15.0 mmol) was added dropwise, at which time all the acid went into solution. The reaction was then removed from the ice bath and heated to reflux for 3.5 h. The reaction mixture was concentrated in vacuo and the resulting solid (1.10 g) was used in the next step without further purification. MS, m/z 159.9=M+1.
Workup
- temperaturecooled in an ice bath
- customThe reaction was then removed from the ice bath
- temperatureheated
- temperatureto reflux for 3.5 h
- concentrationThe reaction mixture was concentrated in vacuo
- customthe resulting solid (1.10 g) was used in the next step without further purification
Sources & evidence
- ORD record
- ord-6fca94d43be24b1f931bf19ece4f82ae
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265132B2
Reaction notes
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