57653-38-0

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-
• CAS NO: 57653-38-0
• Molecular Formula: C21H23NO7S
• Molecular Weight: 433.482
• Mol File: 57653-38-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-(57653-38-0)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-[[(4-methylphenyl)sulfonyl]oxy]-, 2-methyl 1-(phenylmethyl) ester, (2S,4R)-(57653-38-0)

Safety Data

• Hazardous Substances Data: 57653-38-0(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 2232-08-8 N-tosylimidazole 
• 98-59-9 p-toluenesulfonyl chloride 
• 186581-53-3 diazomethane 

Downstream Products

• 20182-95-0 cis-4-methylsulfanyl-L-proline 
• 102013-10-5 (2S,4R)-1-[(benzyloxy)carbonyl]-4-(p-toluenesulfonyloxy)pyrrolidine-2-formic acid 
• 1279200-14-4 C₁₃H₁₈N₂O₃ 
• 756846-17-0 (4R)-N-benzyloxycarbonyl-4-(4-toluenesulfonyloxy)-L-prolyl chloride 
• 279-33-4 (1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]heptane 
• 57653-36-8 (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-(tosyloxy)pyrrolidine 
• 86965-82-4 trans-4-(toluene-4-sulfonyloxy)-proline 
• 83552-05-0 (2S,4S)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-4-phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester 
• 83552-06-1 [1(S),4S]-1-[N-(1-Carboxy-3-phenylpropyl)-L-alanyl]-4-(phenylthio)-L-prolin 
• 105107-84-4 (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid; hydrobromide 
• 83552-04-9 (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride 

Relevant articles and documents

Preparation method for (1S,4S)-2,5-diazabicyclo[2.2.1]heptane or (1S,4S)-2,5-diazabicyclo [2.2.1]octane derivative

The invention discloses a preparation method for a (1S,4S)-2,5-diazabicyclo[2.2.1]heptane or (1S,4S)-2,5-diazabicyclo [2.2.1]octane derivative. The method comprises the following steps: subjecting a hydroxyl group of five-component or six-component N-heterocycle to sulfonylation by using a sulfonylation reagent; then subjecting sulfonate to a substitution reaction of SN2 by using an azide; simultaneously reducing an azido group and an ester group by using a reduction reaction; and finally, carrying out ring closure so as to obtain the derivative. The synthesis route of the preparation method has higher selectivity compared with the prior art; reaction steps are reduced; cost for raw materials and time cost are saved; product yield is substantially higher than product yield in the prior art; and the preparation method can easily realize purification and enlarged production and reduce discharging of waste.

An improved synthesis of (lS,4S)-2-oxa-5-azabicyclo[2.2.1]heptane

An improved and efficient method for synthesis of (lS,4S)-2-oxa-5- azabicyclo[2.2.1]heptane (1) from trans-4-hydroxy-l-proline was developed. Using benzyloxycarbonyl (Cbz) as protection group of amine, the reactions were in mild conditions, and the title compound 1 was accomplished in six steps in overall yield of 70%.

Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists

A series of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives were synthesized and evaluated for their activity as VLA-4 antagonists. Of 22 compounds synthesized, 19 compounds showed potent activity with low nanomolar IC50 values. In addition, the representative compounds 11o and 11p with a hydroxy group in the pyrrolidine ring showed moderate plasma clearance in rats (11o, 30 ml/min/kg and 11p, 21 ml/min/kg) and in dogs (11o, 12 ml/min/kg and 11p, 9 ml/min/kg).