N-Cbz-L-Leucine synthesis
- Product Name:N-Cbz-L-Leucine
- CAS Number:2018-66-8
- Molecular formula:C14H19NO4
- Molecular Weight:265.3
51021-87-5
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2018-66-8
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Yield:2018-66-8 82%
Reaction Conditions:
with water;lithium hydroxide in tetrahydrofuran at 20; for 1.5 h;
Steps:
IX.3 ((Benzyloxy)carbonyl)-L-leucine (118)
To a solution of compound 117 (430 mg, 1.54 mmol) in THF (10 mL) was added LiOH (1M, 1.85 mL, 1.85 mmol). The reaction mixture was stirred for 1.5 h at room temperature. The pH of the solution was then adjusted to ~1-2 by addition of 1N HCl. The reaction mixture was extracted with ethyl acetate, dried over Na2SO4, filtrated and concentrated to give compound 118 (335 mg, 82%). 1H NMR (400 MHz, Chloroform-d) d 10.20 (s, 1H), 7.49- 7.30 (m, 6H), 5.26- 5.06 (m, 3H), 4.42 (td, J = 9.1, 4.7 Hz, 1H), 1.85- 1.64 (m, 2H), 1.56 (ddd, J = 13.4, 9.4, 5.3 Hz, 1H). 13C NMR (101 MHz, CDCl3) d 178.24, 156.15, 136.10, 128.55, 128.24, 128.12, 67.19, 52.39, 41.46, 24.77, 22.83, 21.73. ESI-MS (m/z): 266.1 (M + H)+.
References:
EMORY UNIVERSITY;SCHINAZI, Raymond F.;ZANDI, Keivan;AMBLARD, Franck WO2020/247665, 2020, A1 Location in patent:Page/Page column 146
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2018-66-8
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16881-37-1
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2018-66-8
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13139-17-8
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61-90-5
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2018-66-8
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