(s)-2-Piperidinone-6-carboxylic acid

Base Information

• Chemical Name: (s)-2-Piperidinone-6-carboxylic acid
• CAS No.: 34622-39-4
• Molecular Formula: C6H9NO3
• Molecular Weight: 143.142
• Hs Code.: 2933790090
• European Community (EC) Number: 628-449-3
• Nikkaji Number: J1.205.264B
• Mol file: 34622-39-4.mol

Synonyms:34622-39-4;(s)-2-piperidinone-6-carboxylic acid;(2S)-6-oxopiperidine-2-carboxylic acid;L-6-Oxo-pipecolinic acid;(S)-6-oxopiperidine-2-carboxylic acid;(S)-6-Oxo-2-piperidinecarboxylic acid;(S)-6-Oxo-piperidine-2-carboxylic acid;(S)-PIPERIDINONE-6-CARBOXYLIC ACID;MFCD03839863;2-Piperidinecarboxylic acid, 6-oxo-, (S)-;Pyrohomoglutamic acid, L-;L-PYROHOMOGLUTAMIC ACID;SCHEMBL3625069;FZXCPFJMYOQZCA-BYPYZUCNSA-N;AKOS015995273;AC-6731;CS-W018258;GS-4111;A6085;AM20090542;Q-103017;(S)-6-Oxo-2-piperidinecarboxylic acid, >=95.0% (HPLC);B205413C-614F-44EA-9706-2BBC48FC4F76

Chemical Property of (s)-2-Piperidinone-6-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 129-134 °C
• Refractive Index: 1.499
• Boiling Point: 436.964 °C at 760 mmHg
• PKA: 3.59±0.20(Predicted)
• Flash Point: 218.068 °C
• PSA: 66.40000
• Density: 1.287 g/cm³
• LogP: 0.06850
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Aqueous Acid (Sparingly, Heated, Sonicated), DMSO (Slightly, Heated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

6-Oxo-L-pipecolicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(NC(=O)C1)C(=O)O
• Isomeric SMILES: C1C[C@H](NC(=O)C1)C(=O)O
• Uses: 6-Oxo-L-pipecolic Acid is an intermediate in the synthesis of metabolites of lysine developed during aging and in diabetic patients. (S)-6-Oxo-2-piperidinecarboxylic acid can be used as a reactant to synthesize: Functionalized β-lactam N-heterocycles via carboxymethylproline synthase catalyzed cyclization reactions. Pro-(S)-C5 branched [4.3.1] aza-amide bicycles as potential inhibitors for FK506-binding proteins. Ethyl (S)-2-(6-oxopiperidin-2-yl)acetate, which is reduced using LiBH4 to produce optically pure hydroxymethyl lactams.

Technology Process of (s)-2-Piperidinone-6-carboxylic acid

There total 16 articles about (s)-2-Piperidinone-6-carboxylic acid 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: 94.0%

L-homoglutamic acid (1118-90-7) → (2S)-6-oxopipecolic acid (34622-39-4)

Guidance literature:

With acetic acid; for 6h; Heating;

DOI:10.1248/cpb.47.1525

Reference yield:

Z-Lys(Boc)-OH (2389-60-8) → (2S)-6-oxopipecolic acid (34622-39-4)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

2: CH₂Cl₂ / 1 h / Ambient temperature

3: 93 percent / TFA / 10 - 15 °C

4: 1.) 4-formyl-1-methylpyridinium benzenesulfonate, 2.) DBU, 3.) aq. oxalic acid / 1) CH₂Cl₂, DMF, room temperature; 2) 5 min; 3) cooling, 0.5 - 1 h

5: 1.) Jones reagent, 2.) aq. HCl / 1) room temperature, acetone; 2) heating

6: 85 percent / 0.5 h / 170 °C

With hydrogenchloride; jones reagent; oxalyl dichloride; oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridinium-4-carboxaldehyde benzenesulfonate salt; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00380a019

Reference yield:

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) → (2S)-6-oxopipecolic acid (34622-39-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / aq. alkali

2: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

3: CH₂Cl₂ / 1 h / Ambient temperature

4: 93 percent / TFA / 10 - 15 °C

5: 1.) 4-formyl-1-methylpyridinium benzenesulfonate, 2.) DBU, 3.) aq. oxalic acid / 1) CH₂Cl₂, DMF, room temperature; 2) 5 min; 3) cooling, 0.5 - 1 h

6: 1.) Jones reagent, 2.) aq. HCl / 1) room temperature, acetone; 2) heating

7: 85 percent / 0.5 h / 170 °C

With hydrogenchloride; jones reagent; oxalyl dichloride; oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridinium-4-carboxaldehyde benzenesulfonate salt; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00380a019

upstream raw materials:

L-homoglutamic acid

(S)-2-amino-6-hydroxyhexanoic acid

N₆-[(benzyloxy)carbonyl]-L-lysine

(2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid

Downstream raw materials:

diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate

diphenylmethyl N-phenoxycarbonyl-6-oxopipecolate

diphenylmethyl N-tert-butoxycarbonyl-6-oxopipecolate

benzyl N-benzyloxycarbonyl-6-oxopipecolate

Refernces

• 1、 -. "THERAPEUTICALLY ACTIVE COMPOUNDS AND USE THEREOF". Page/Page column 93. . Retrieved 2015/02/19.
• 2、 -. "HEPATITIS C VIRUS INHIBITORS". Paragraph 0295; 0296. . Retrieved 2013/11/06.