902146-43-4

Basic information

• Product Name: (S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide
• Synonyms: -2-Benzyl-N,N-dimethylaziridine-1-sulfonamide;N,N-Dimethyl-2-Benzyl-(2S)-1-Aziridinesulfonamide
• CAS NO: 902146-43-4
• Molecular Formula: C₁₁H₁₆N₂O₂S
• Molecular Weight: 240.32194
• EINECS: 1806241-263-5
• Mol File: 902146-43-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 367.882 °C at 760 mmHg
• Flash Point: 176.289 °C
• Appearance: /
• Density: 1.285 g/cm³
• Storage Temp.: 2-8°C
• PKA: -4.63±0.70(Predicted)
• CAS DataBase Reference: (S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide(902146-43-4)
• EPA Substance Registry System: (S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide(902146-43-4)

Safety Data

• Hazardous Substances Data: 902146-43-4(Hazardous Substances Data)

Usage

General Description

(S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide is a chemical compound that belongs to the class of sulfonamide compounds. It is a chiral reagent that is commonly used in organic synthesis for the asymmetric synthesis of various compounds. (S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide has a unique structure with a sulfonamide moiety, which makes it a valuable building block for the preparation of complex organic molecules. The benzyl and dimethyl groups on the aziridine ring also contribute to the compound's chemical properties and reactivity. Due to its versatile nature, (S)-2-Benzyl-N,N-diMethylaziridine-1-sulfonaMide has found applications in the pharmaceutical industry, as well as in academic research for the development of new drug candidates and bioactive molecules.

InChI:InChI=1S/C11H16N2O2S/c1-12(2)16(14,15)13-9-11(13)8-10-6-4-3-5-7-10/h3-7,11H,8-9H2,1-2H3/t11-,13?/m0/s1

Synthetic route

(2S)-2-benzylazacyclopropane (73058-30-7) + dimethylamino sulfonyl chloride (13360-57-1) → (D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	78%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 16h;	77%
With triethylamine In n-heptane; tert-butyl methyl ether at 0℃; for 18h; Time;	60%

C11H18N2O3S (1178000-69-5) → (D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate; p-toluenesulfonyl chloride In dichloromethane at 0 - 25℃;	67.56%

C13H23N3O5S2 (1247119-25-0) → (D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4)

Conditions	Yield
With sodium hydride In 2-methyltetrahydrofuran at 0 - 20℃;	64%

L-Phenylalaninol (3182-95-4) → (D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 62 percent / DIAD; PPh3 / toluene / Heating 2: 78 percent / Et3N / CH2Cl2 / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / Reflux 2: tetrabutylammomium bromide; potassium carbonate; p-toluenesulfonyl chloride / dichloromethane / 0 - 25 °C View Scheme

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → (D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate / water / 16 h / 0 - 5 °C 1.2: pH 5 1.3: 3 h / Reflux 2.1: triethylamine / dichloromethane / Reflux 3.1: tetrabutylammomium bromide; potassium carbonate; p-toluenesulfonyl chloride / dichloromethane / 0 - 25 °C View Scheme

D-(R)-phenylalanine (673-06-3) → (D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; zinc(II) chloride / 1,4-dioxane / 70 °C 2: sulfuric acid / toluene / 110 - 120 °C 3: triethylamine / tert-butyl methyl ether; n-heptane / 18 h / 0 °C View Scheme

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + aniline (62-53-3) → C17H23N3O2S

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	90%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + propylamine (107-10-8) → (4S)-4-benzyl-2-propyl-1,2,5-thiadiazolidine-1,1-dioxide

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	87%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + 2-methoxyethylamine (109-85-3) → (S)-4-Benzyl-2-(2-methoxy-ethyl)-[1,2,5]thiadiazolidine 1,1-dioxide

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	81%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + 1-amino-2-propene (107-11-9) → (S)-2-Allyl-4-benzyl-[1,2,5]thiadiazolidine 1,1-dioxide

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	77%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + tert-butylamine (75-64-9) → 4-benzyl-2-tert-butyl-[1,2,5]thiadiazolidine 1,1-dioxide

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	67%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + 3-Aminomethylpyridine (3731-52-0) → 3-((S)-4-Benzyl-1,1-dioxo-1λ6-[1,2,5]thiadiazolidin-2-ylmethyl)-pyridine

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	66%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + Cyclopropylamine (765-30-0) → (S)-4-Benzyl-2-cyclopropyl-[1,2,5]thiadiazolidine 1,1-dioxide

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	66%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) + 4-methoxy-benzylamine (2393-23-9) → (4S)-4-benzyl-2-(4-methoxybenzyl)-1,2,5-thiadiazolidine-1,1-dioxide (902146-60-5)

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 16h;	64%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) → C22H32N4O4S2

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -10 - 0℃; Product distribution / selectivity;	64%

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) → (3S)-3-benzyl-2-propyl-1,2,5-thiadiazolidine-1,1-dioxide

Conditions	Yield
Multi-step reaction with 3 steps 1: 64 percent / dimethylsulfoxide / 16 h / 100 °C 2: 96 percent / NaH / dimethylformamide / 1 h 3: 99 percent / TFA / 2 h / 20 °C View Scheme

(D)-2-benzyl-N,N-dimethylaziridinyl-1-sulfonamide (902146-43-4) → (3S)-3-benzyl-5-(4-methoxybenzyl)-2-propyl-1,2,5-thiadiazolidine-1,1-dioxide (902146-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / dimethylsulfoxide / 16 h / 100 °C 2: 96 percent / NaH / dimethylformamide / 1 h View Scheme

Upstream product

• 673-06-3 D-(R)-phenylalanine 
• 1178000-69-5 C₁₁H₁₈N₂O₃S 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1247119-25-0 C₁₃H₂₃N₃O₅S₂ 
• 3182-95-4 L-Phenylalaninol 
• 73058-30-7 (2S)-2-benzylazacyclopropane 
• 13360-57-1 dimethylamino sulfonyl chloride 

Downstream Products

• 902146-62-7 (3S)-3-benzyl-5-(4-methoxybenzyl)-2-propyl-1,2,5-thiadiazolidine-1,1-dioxide 

Relevant articles and documents

Synthesis method of (D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide

The invention discloses a synthesis method of (D)-2-benzyl-N,N-dimethylaziridine-1-sulfonamide, which comprises the following steps: a. reducing D-phenylalanine to obtain D-phenylalaninol, b. performing esterification and ring-closing reactions on the D-phenylalaninol to obtain (D)-2-benzyl-N,N-dimethylaziridine; and c. carrying out a reaction on the (D)-2-benzyl-N,N-dimethylaziridine with dimethylamino sulfonyl chloride to generate the (D)-2-benzyl-N,N-dimethyl aziridine-1-sulfonamide. The product has high content and purity, enhances the yield of industrial production, shortens the half timeof industrial production, and effectively considers the problems of environmental protection, cost and yield.

METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS

The invention provides methods and intermediates that are useful for preparing a compound of formula I: and salts thereof.