N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide
• CAS No.: 459457-14-8
• Molecular Formula: C₁₃H₁₈INO₄S
• Molecular Weight: 411.261
• Mol file: 459457-14-8.mol

Synonyms:N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

Chemical Property of N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

There total 11 articles about N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 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: 86.0%

N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-08-0) → N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-14-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1016/S0040-4039(02)00833-X

Reference yield:

(2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid (34235-88-6) → N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-14-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: KHCO₃ / dimethylformamide

2.1: LiBH₄ / tetrahydrofuran

3.1: TsOH / CH₂Cl₂

4.1: 96 percent / NaH / dimethylformamide

5.1: OsO₄; NMO / acetone; H₂O

5.2: NaIO₄ / tetrahydrofuran; various solvent(s)

5.3: 100 percent / NaBH₄ / methanol

6.1: 97 percent / I₂; Ph₃P; imidazole / toluene

7.1: aq. HCl; tetrahydrofuran

8.1: imidazole / dimethylformamide

9.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂

10.1: 86 percent / HF / acetonitrile

With 1H-imidazole; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; hydrogen fluoride; iodine; sodium hydride; potassium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(02)00833-X

Reference yield:

(2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate (43188-53-0) → N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide (459457-14-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: LiBH₄ / tetrahydrofuran

2.1: TsOH / CH₂Cl₂

3.1: 96 percent / NaH / dimethylformamide

4.1: OsO₄; NMO / acetone; H₂O

4.2: NaIO₄ / tetrahydrofuran; various solvent(s)

4.3: 100 percent / NaBH₄ / methanol

5.1: 97 percent / I₂; Ph₃P; imidazole / toluene

6.1: aq. HCl; tetrahydrofuran

7.1: imidazole / dimethylformamide

8.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂

9.1: 86 percent / HF / acetonitrile

With 1H-imidazole; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; hydrogen fluoride; iodine; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; hydrogenchloride; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/S0040-4039(02)00833-X

upstream raw materials:

N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide

(2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)butanoic acid

(2S,3R)-methyl-N-(4-methylphenylsulfonyl)-3-hydroxy-2-aminobutanoate

p-toluenesulfonyl chloride

Downstream raw materials:

(2S,3R)-3-hydroxy-3-methylpyrrolidine-2-carboxylic acid

(2R,3R)-2-hydroxymethyl-3-methyl-1-(toluene-4-sulfonyl)pyrrolidin-3-ol