N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Base Information

• Chemical Name: N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide
• CAS No.: 108591-33-9
• Molecular Formula: C₁₆H₁₉NO₃S
• Molecular Weight: 305.398
• Mol file: 108591-33-9.mol

Synonyms:N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Chemical Property of N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide

There total 69 articles about N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8) + p-toluenesulfonyl chloride (98-59-9) → N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1002/ejoc.200700763

Reference yield: 96.0%

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) + p-toluenesulfonyl chloride (98-59-9) → N-[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]-4-methylbenzenesulfonamide (58107-41-8,58107-43-0,108591-33-9,131142-88-6,143957-01-1,136173-99-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 12h;

DOI:10.1016/S0957-4166(98)00155-4

Reference yield: 93.0%

acetic acid tert-butyl ester (540-88-5) + 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester (594836-47-2) → (R)-tert-butyl 2-(tert-butylsulfinyl)acetate + N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-4-methylbenzene sulfonamide (108591-33-9)

Guidance literature:

acetic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -45 ℃; for 0.5h;

2-Methyl-propane-2-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester; In tetrahydrofuran; hexane; at -78 - -10 ℃;

DOI:10.1016/j.tet.2005.03.122

upstream raw materials:

1.3-propanedithiol

(R)-2-[(2R,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propan-1-ol

(R)-2-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propan-1-ol

(1R,2S)-norephedrine

Downstream raw materials:

(S)-2-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

(R)-2-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone

(2S,4S,5R)-4-methyl-5-phenyl-2-(1-phenyl-vinyl)-3-(toluene-4'-sulfonyl)-oxazolidine

(S)-4-methyl-N-(1-methyl-2-oxo-2-phenyl-ethyl)-benzenesulfonamide

Refernces

• 1、 Michelet, Bastien,Castelli, Ugo,Appert, Emeline,Boucher, Maude,Vitse, Kassandra,Marrot, Jér?me,Guillard, Jér?me,Martin-Mingot, Agnès,Thibaudeau, Sébastien. "Access to Optically Pure Benzosultams by Superelectrophilic Activation". supporting information. p. 4944 - 4948. Retrieved 2020/07/14.
• 2、 Yang, Hui,Zheng, Wen-Hua. "Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols". supporting information. p. 16177 - 16180. Retrieved 2019/11/03.