L-tert-Leucine methyl ester hydrochloride synthesis
- Product Name:L-tert-Leucine methyl ester hydrochloride
- CAS Number:63038-27-7
- Molecular formula:C7H16ClNO2
- Molecular Weight:181.66
67-56-1
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63038-27-7
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Yield:63038-27-7 100%
Reaction Conditions:
with thionyl chloride for 16 h;Reflux;
Steps:
(S)-Methyl 2-amino-3,3-dimethylbutanoate hydrochloride 37
To a solution of l-tert-leucine (1.0 g, 7.7 mmol) in methanol (60 mL) was added thionyl chloride (5.6 mL, 77 mmol) and the mixture was heated at reflux for 16 hours. The volatiles were removed under reduced pressure and the residue triturated with diethyl ether to obtain a white solid that was collected by filtration and dried in vacuo to obtain the title compound 37 (1.1 g, 100%) as a gummy, white hygroscopic solid, IR (vmax (neat)): 3383, 2961, 2365, 1735, 1613, 1517, 1248 cm-1; 1H NMR (300 MHz, DMSO-d6): δ 1.00 (9H, s), 3.66 (1H, s), 8.31-9.00 (3H, m) ppm; 13C NMR (75 MHz, DMSO-d6): 26.3, 33.1, 52.3, 60.7, 168.8 ppm; LRMS (+ESI) m/z: 146.1 ([M+H]+ 100%).
References:
Moir, Michael;Lane, Samuel;Lai, Felcia;Connor, Mark;Hibbs, David E.;Kassiou, Michael [European Journal of Medicinal Chemistry,2019,vol. 180,p. 291 - 309] Location in patent:supporting information
67-56-1
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62965-35-9
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63038-27-7
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67-56-1
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139163-43-2
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63038-27-7
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75158-11-1
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63038-27-7
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630-19-3
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63038-27-7
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