ChemicalBook > CAS DataBase List > (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane

(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
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(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)
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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.

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N-Bromosuccinimide Price

AK Scientific
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
American Custom Chemicals Corporation
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
Ambeed
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
Ambeed
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
Ambeed
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
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(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

Preparation Products

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(2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane Suppliers

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162536-40-5, (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutaneRelated Search:

tert-butyl(4-(3-(dimethoxyphosphoryl)-2-oxopropyl)phenyl)carbamate tert-butyl 7-chloro-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate (2R,3S)-3-(tert-Butoxycarbonyl)amino-1,2-epoxy-4-phenylbutane (2S,3S)-3-(Benzyloxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane (2R)-4-(PhenylMethyl)-2-MorpholineMethanaMine (2R,5R)-2,5-DIMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER (2R,5R)-1,6-Diphenylhexane-2,5-diaMine dihydrochloride 2-Pyrrolidinecarbonitrile,(2R)- Benzeneacetic acid, alpha-amino-alpha-methyl-, (alphaR)- (9CI) N-BOC-3-CHLOROPROPYLAMINE (2R,3S)-3-(tert-Butoxycarbonylamino)-1-chloro-2-hydroxy-4-phenylbutane [1(S)-(4-BENZYLOXY-BENZYL)-3-CHLORO-2(R)-HYDROXY-PROPYL]-CARBAMIC ACID TERT-BUTYL ESTER [1(S)-(4-NITRO-BENZYL)-3-CHLORO-2(R)-HYDROXY-PROPYL]-CARBAMIC ACID TERT-BUTYL ESTER

  • (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...
  • (2R,3S)-2-Hydroxy-3-((tert-butoxycarbonyl)amino)-4-phenyl-1-chlorobutane
  • 162536-40-5
  • API intermediates