(2S)-1,2-dimethylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S)-1,2-dimethylpyrrolidine-2-carboxylic acid
• CAS No.: 1268519-85-2
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.186
• DSSTox Substance ID: DTXSID201314472
• Mol file: 1268519-85-2.mol

Synonyms:dimethylproline;proline betaine;stachydrine;stachydrine chloride;stachydrine chloride, (S)-isomer;stachydrine, (+-)-isomer

Chemical Property of (2S)-1,2-dimethylpyrrolidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 226.3±33.0 °C(Predicted)
• PKA: 2.52±0.20(Predicted)
• PSA: 40.54000
• Density: 1.097±0.06 g/cm3(Predicted)
• LogP: 0.49320
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 158

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCCN1C)C(=O)O
• Isomeric SMILES: C[C@]1(CCCN1C)C(=O)O

Technology Process of (2S)-1,2-dimethylpyrrolidine-2-carboxylic acid

There total 2 articles about (2S)-1,2-dimethylpyrrolidine-2-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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (S)-2-methylpyrrolidine-2-carboxylic acid (42856-71-3) → (S)-1,2-dimethyl-pyrrolidine-2-carboxylic acid (1268519-85-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; for 48h; under 1551.49 Torr;

Reference yield:

(S)-2-methylpyrrolidine-2-carboxylic acid (42856-71-3) → (S)-1,2-dimethyl-pyrrolidine-2-carboxylic acid (1268519-85-2)

Guidance literature:

With formaldehyd; hydrogen; In methanol; dichloromethane; water;

Reference yield: 69.0%

(S)-1,2-dimethyl-pyrrolidine-2-carboxylic acid (1268519-85-2) + methyl (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate (669074-47-9) → 1,2-dimethyl-L-prolyl-N-{(1S,2R)-4-{(2S)-2-[(1R,2R)-3-{[(1S)-1-carboxy-2-phenylethyl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl}-N-methyl-L-valinamide

Guidance literature:

(S)-1,2-dimethyl-pyrrolidine-2-carboxylic acid; methyl (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate; With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20 ℃; for 1h;

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 1.5h;

upstream raw materials:

(S)-2-methylpyrrolidine-2-carboxylic acid

formaldehyd

Refernces

• 1、 -. "CYTOTOXIC PEPTIDES AND ANTIBODY DRUG CONJUGATES THEREOF". Page/Page column 190. . Retrieved 2013/06/05.