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| | (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Basic information |
| Product Name: | (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane | | Synonyms: | (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane;Carbamic acid, N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane;(2R,3S)-N-tert-Butoxycarbonyl-3-amino-1-chloro-2-hydroxy-4-phenylbutane;N-[(1S,2R)-3-Chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester;tert-Butyl ((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbaMate;tert-butyl N-[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate;(2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-ph... | | CAS: | 162536-40-5 | | MF: | C15H22ClNO3 | | MW: | 299.79 | | EINECS: | 923-366-1 | | Product Categories: | API intermediates | | Mol File: | 162536-40-5.mol |  |
| | (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Chemical Properties |
| Melting point | 83-84℃ | | Boiling point | 460.5±45.0 °C(Predicted) | | density | 1.153 | | storage temp. | 2-8°C | | pka | 11.92±0.46(Predicted) |
| | (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Usage And Synthesis |
| Synthesis | The synthesis of tert-butyl (1S,2S)-(1-benzyl-3-chloro-2-hydroxypropyl)carbamate and (2R,3S)-3-tert-butoxycarbonyl-1-chloro-2-hydroxy-4-phenylbutane was carried out via ruthenium-catalyzed asymmetric hydrogenation using (3S)-3-(tert-butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone as the starting material. The experiments were catalyzed using different ruthenium ligands under the following reaction conditions: substrate 1 mmol, substrate to catalyst ratio (S/C) of 100:1, solvent 4 mL methanol, and reaction time 20 h (not optimized). The reaction temperature and pressure were adjusted according to the catalyst type, and the results are shown in Table 1.Entry 1 used Ru(S-Xyl-P-Phos)(acac) as the catalyst and was reacted at 50 °C and 1 bar pressure, resulting in a conversion of 51%, with the major product in the (2R,3S)-configuration, and an enantiomeric excess (de) of 82%.Entry 2 used Ru(SP -Phos)Cl2(dmf) as a catalyst at 65 °C and 20 bar pressure resulted in 89% conversion with the same (2R,3S)-configuration as the major product and an enantiomeric excess (de) of 79%. | | References | [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 12, p. 1758 - 1768
[2] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7344 - 7347
[3] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7391 - 7394 |
| | (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Preparation Products And Raw materials |
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