(S)-3-(Tosylamino)-2-piperidone

Base Information

• Chemical Name: (S)-3-(Tosylamino)-2-piperidone
• CAS No.: 124288-95-5
• Molecular Formula: C₁₂H₁₆N₂O₃S
• Molecular Weight: 268.337
• European Community (EC) Number: 694-549-9

Synonyms:124288-95-5;(S)-4-Methyl-N-(2-oxopiperidin-3-yl)benzenesulfonamide;4-methyl-N-[(3S)-2-oxopiperidin-3-yl]benzenesulfonamide;(S)-3-(Tosylamino)-2-piperidone;starbld0001932;SCHEMBL14855597;(S)-3-(Tosylamino)-2-piperidone, 97%

Chemical Property of (S)-3-(Tosylamino)-2-piperidone

Chemical Property:

• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 268.08816355
• Heavy Atom Count: 18
• Complexity: 394

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC2CCCNC2=O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@H]2CCCNC2=O

Technology Process of (S)-3-(Tosylamino)-2-piperidone

There total 8 articles about (S)-3-(Tosylamino)-2-piperidone 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: 29.0%

L-ornithine hydrochloride (3184-13-2,36630-89-4) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(2-oxopiperidin-3-yl)benzenesulfonamide (124288-95-5)

Guidance literature:

L-ornithine hydrochloride; With acetyl chloride; In methanol; at 65 ℃; for 12h;

With triethylamine; In methanol; at 65 ℃; for 2h;

p-toluenesulfonyl chloride; With pyridine; In dichloromethane; at 23 ℃; for 8h;

DOI:10.1021/ja8031955

Reference yield:

α-N-tosyl-δ-N-carbobenzoxyornthine (110414-90-9) → 4-methyl-N-(2-oxopiperidin-3-yl)benzenesulfonamide (124288-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / CHCl₃ / 22 h / 22 °C

2: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

3: 22 °C

With hydrogen; palladium on activated charcoal; In methanol; chloroform;

DOI:10.1021/jo00290a028

Reference yield:

1,1-dimethylethyl (S)-2-<<(4-methylphenyl)sulfonyl>-amino>-5-<<(phenylmethoxy)carbonyl>amino>pentanoate (124288-73-9) → 4-methyl-N-(2-oxopiperidin-3-yl)benzenesulfonamide (124288-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / H₂ / 10percent Pd/C / methanol / 3102.9 Torr

2: 22 °C

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00290a028

upstream raw materials:

N⁵-benzyloxycarbonyl-N²-(toluene-4-sulfonyl)-L-ornithine amide

N²-(toluene-4-sulfonyl)-L-ornithine methyl ester; hydrochloride

1,1-dimethylethyl (S)-5-amino-2-<<(4-methylphenyl)sulfonyl>-amino>pentanoate

α-N-tosyl-δ-N-carbobenzoxyornthine

Downstream raw materials:

N²-(toluene-4-sulfonyl)-L-ornithine

L-ornithine

L-arginine

N^α-p-tosyl-L-arginine

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