Simple and Efficient Synthesis of Racemic 2-(tert-Butoxycarbon-ylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic Acid, a New Derivative of β-(1,2,4-Triazol-1-yl)alanine
Abstract
:1. Introduction
2. Results and Discussion
Position | δH | δC | Correlation 1H-1H | Correlation 1H-13C |
---|---|---|---|---|
(NH) 1 | 6.29 (s) | - | 1-H | - |
2 | - | 56.66 | - | - |
3 | 3.35, 3.45 (AB (2dd), 10.8; 5.6) | 64.85 | H1-3, H2-3, O-H | H1-3, H2-3, C-3 |
(OH) 4 | 4.92 (t, 5.6) | - | O-H, H1-3, H2-3 | - |
5 | 1.18 (s) | 20.43 | H1-5, H2-5, H3-5 | H1,2,3-5; C-5 |
6 | 4.35, 4.51 (AB, 14) | 51.74 | H1-6, H2-6 | H1-6, H2-6, C-6 |
9 | 7.95 (s) | 151.61 | H3'triazole -9 | H3'triazole -9, C-9 |
11 | 8.23 (s) | 145.24 | H5'-triazole -11 | H5'-triazole -11, C-11 |
12 | - | 154.97 | - | - |
14 | - | 78.43 | - | - |
H1,2,3-15 | H1,2,3-15; C-15 | |||
15; 17; 18 | 1.39 (s) | 28.68 | H1,2,3-17 | H1,2,3-17; C-17 |
H1,2,3-18 | H1,2,3-18; C-18 |
Position | δH | δN | Correlation 1H-15N |
---|---|---|---|
1 (HN) | 7.02 (s) | 94.23 | H-1,N-1 |
5 | 1.24 (s) | 93.29 | H1,2,3-5, N-1 |
6 | 4.39, 4.83 (AB, 14) | 93.03 | H1,2-6, N-1 |
214.36 | H1,2-6, N-7 | ||
299.27 | H1,2-6, N-8 | ||
9 | 7.96 (s) | 214.58 | H3'triazole-9, N-7 |
252.01 | H3'triazole-9, N-10 | ||
299.06 | H3'triazole-9, N-8 | ||
11 | 8.20 (s) | 214.58 | H5'-triazole-11, N-7 |
252.01 | H5'-triazole-11, N-10 |
Position | δH | δC | Correlation 1H-1H | Correlation 1H-13C |
---|---|---|---|---|
(NH)1 | 7.02 (s) | - | 1-H | - |
2 | - | 58.24 | - | - |
3 | - | 174.53 | - | - |
(OH)4 | 12.73 (br, s) | - | - | - |
5 | 1.24 (s) | 22.33 | H1-5, H2-5, H3-5 | H1,2,3-5; C-5 |
6 | 4.39, 4.83 (AB, 14) | 52.06 | H1-6, H2-6 | H1-6, H2-6, C-6 |
9 | 7.96 (s) | 151.63 | H3'triazole -9 | H3'triazole -9, C-9 |
11 | 8.20 (s) | 145.56 | H5'-triazole -11 | H5'-triazole -11, C-11 |
12 | - | 155.02 | - | - |
14 | - | 78.95 | - | - |
H1,2,3-15 | H1,2,3-15; C-15 | |||
15; 17; 18 | 1.40 (s) | 28.64 | H1,2,3-17 | H1,2,3-17; C-17 |
H1,2,3-18 | H1,2,3-18; C-18 |
3. Experimental
3.1. General
3.2. 4-((1H-1,2,4-Triazol-1-yl)methyl)-4-methyl-2-phenyl-4,5-dihydrooxazole (2)
3.3. 2-Amino-2-methyl-3-(1H-1,2,4-triazol-1-yl)propan-1-ol hydrochloride (3)
3.4. tert-Butyl[1-hydroxy-2-methyl-3-(1H-1,2,4-triazol-1-yl)]propan-2-ylcarbamate (4)
3.5. 2-(tert-Butoxycarbonylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic acid (5)
4. Conclusions
Acknowledgements
References and Notes
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- Sample Availability: Samples of the compounds 1-5 are available from the authors.
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Aouine, Y.; Faraj, H.; Alami, A.; El-Hallaoui, A.; Elachqar, A.; Kerbal, A. Simple and Efficient Synthesis of Racemic 2-(tert-Butoxycarbon-ylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic Acid, a New Derivative of β-(1,2,4-Triazol-1-yl)alanine. Molecules 2011, 16, 3380-3390. https://doi.org/10.3390/molecules16043380
Aouine Y, Faraj H, Alami A, El-Hallaoui A, Elachqar A, Kerbal A. Simple and Efficient Synthesis of Racemic 2-(tert-Butoxycarbon-ylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic Acid, a New Derivative of β-(1,2,4-Triazol-1-yl)alanine. Molecules. 2011; 16(4):3380-3390. https://doi.org/10.3390/molecules16043380
Chicago/Turabian StyleAouine, Younas, Hassane Faraj, Anouar Alami, Abdelilah El-Hallaoui, Abdelrhani Elachqar, and Abdelali Kerbal. 2011. "Simple and Efficient Synthesis of Racemic 2-(tert-Butoxycarbon-ylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic Acid, a New Derivative of β-(1,2,4-Triazol-1-yl)alanine" Molecules 16, no. 4: 3380-3390. https://doi.org/10.3390/molecules16043380