(2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane
- Product Name
- (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane
- CAS No.
- 162536-40-5
- Chemical Name
- (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane
- Synonyms
- (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-ph...;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-phenylbutane;(2R,3S)-N-tert-Butoxycarbonyl-3-amino-1-chloro-2-hydroxy-4-phenylbutane;(2R,3S)-2-Hydroxy-3-((tert-butoxycarbonyl)amino)-4-phenyl-1-chlorobutane;(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane;N-[(1S,2R)-3-Chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester;Carbamic acid, N-[(1S,2R)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester
- CBNumber
- CB01512395
- Molecular Formula
- C15H22ClNO3
- Formula Weight
- 299.79
- MOL File
- 162536-40-5.mol
(2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Property
- 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)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 4431CR
- Product name
- Tert-Butyl((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
- Packaging
- 1g
- Price
- $104
- Updated
- 2021/12/16
- Product number
- CCH0006626
- Product name
- (2R,3S)-3-(TERT-BUTOXYCARBONYLAMINO)-1-CHLORO-2-HYDROXY-4-PHENYLBUTANE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $500.24
- Updated
- 2021/12/16
- Product number
- A691852
- Product name
- tert-Butyl((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
- Purity
- 97%
- Packaging
- 250mg
- Price
- $6
- Updated
- 2021/12/16
- Product number
- A691852
- Product name
- tert-Butyl((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
- Purity
- 97%
- Packaging
- 1g
- Price
- $15
- Updated
- 2021/12/16
- Product number
- A691852
- Product name
- tert-Butyl((2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate
- Purity
- 97%
- Packaging
- 5g
- Price
- $44
- Updated
- 2021/12/16
(2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Chemical Properties,Usage,Production
Synthesis
102123-74-0
165727-45-7
162536-40-5
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 Medicinal Chemistry, 1994, vol. 37, # 12, p. 1758 - 1768
[3] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7344 - 7347
[4] Journal of Organic Chemistry, 2004, vol. 69, # 21, p. 7391 - 7394
[5] 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
Raw materials
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