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[ CAS No. 369362-96-9 ] (2R,3S)-3-Amino-1-chloro-4-phenylbutan-2-ol hydrochloride

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Cat. No.: A147159
Chemical Structure| 369362-96-9
Chemical Structure| 369362-96-9
Structure of 369362-96-9
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Product Details of [ 369362-96-9 ]

CAS No. :369362-96-9 MDL No. :N/A
Formula : C10H15Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 236.14 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 369362-96-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 369362-96-9 ]

[ 369362-96-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 369362-96-9 ]
  • [ 24424-99-5 ]
  • [ 165727-45-7 ]
  • [ 162536-40-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In methanol; water; toluene; at 25℃; for 3h;pH 7.0;Product distribution / selectivity; To an aqueous solution of (2R,3S)-3-amino-1-chloro-2-hydroxy-4-phenylbutane hydrochloride (74.4 g) containing its (2S,3S)-form as a diastereomer thereof, which had been obtained in the above-mentioned step (2'f), was added toluene (378 ml), and the mixture was vigorously stirred. The mixture was adjusted to pH 7 with 4 M aqueous sodium hydroxide solution. Keeping pH 7 with 4 M aqueous sodium hydroxide solution, the mixture was added to a mixed solution of di-tert-butyldicarbonate (68.7 g) and toluene (94 ml), and the mixture was vigorously stirred at 25C for 3 hours. The organic layer (606.4 g) was separated, cooled to 0C and filtered. As a result of HPLC analysis, it was found that the filtrate contained (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane (64.9 g, yield 68%), and the diastereomer ratio (2R,3S)/(2S,3S) was 95/5. In addition, the peak area ratio of other byproduct was 19.5% relative to (2R,3S)-3-tert-butoxycarbonylamino-1-chloro-2-hydroxy-4-phenylbutane.
  • 2
  • [ 162536-40-5 ]
  • [ 369362-96-9 ]
YieldReaction ConditionsOperation in experiment
32 g With hydrogenchloride; water; In tetrahydrofuran; at 50 - 55℃; for 4h; Example 1(A): Preparation of f2S.3RV2-Amino-4-chloro-l-phenylbutan-3-ol hydrochloride Formula III To 1 , 1 -dimethylethyl [(2S,3R)-4-chloro-3-hydroxy- l-phenylbutan-2-yl]carbamate (Formula II, 40 g), tetrahydrofuran (200 mL) was added at ambient temperature under stirring. Concentrated hydrochloric acid (27 mL) was slowly added to the mixture. The resultant reaction mixture was heated at 50C to 55C for 4 hours. Tetrahydrofuran was recovered under vacuum from the reaction mixture at 50C to 55C. Water was removed by adding additional tetrahydrofuran (200 mL) to get the semi-solid product. The semisolid product was crystallized with a mixture of ethyl acetate (80 mL) and diisopropyl ether (200 mL) and further stirred for 2 hours at 20C to 25C. The solid so obtained was filtered and dried under vacuum at 40C to 45C to afford the title compound. Weight: 32.0 g Yield (w/w): 0.8
With hydrogenchloride; In tetrahydrofuran; water; at 50 - 55℃; for 4h; Example 1(A) Preparation of (2S,3R)-2-Amino-4-chloro-1-phenylbutan-3-ol hydrochloride To 1,1-dimethylethyl[(2S,3R)-4-chloro-3-hydroxy-1-phenylbutan-2-yl]carbamate (Formula II, 40 g), tetrahydrofuran (200 mL) was added at ambient temperature under stirring. Concentrated hydrochloric acid (27 mL) was slowly added to the mixture. The resultant reaction mixture was heated at 50 C. to 55 C. for 4 hours. Tetrahydrofuran was recovered under vacuum from the reaction mixture at 50 C. to 55 C. Water was removed by adding additional tetrahydrofuran (200 mL) to get the semi-solid product. The semi-solid product was crystallized with a mixture of ethyl acetate (80 mL) and diisopropyl ether (200 mL) and further stirred for 2 hours at 20 C. to 25 C. The solid so obtained was filtered and dried under vacuum at 40 C. to 45 C. to afford the title compound. Weight: 32.0 g
  • 3
  • [ 369362-96-9 ]
  • [ 198904-31-3 ]
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