(S)-(-)-2-Hydroxy-N-methylsuccinimide

Base Information

• Chemical Name: (S)-(-)-2-Hydroxy-N-methylsuccinimide
• CAS No.: 104612-35-3
• Molecular Formula: C5H7NO3
• Molecular Weight: 129.11
• Hs Code.: 2925190090
• European Community (EC) Number: 626-121-4
• DSSTox Substance ID: DTXSID601306198
• Wikidata: Q76423322
• Mol file: 104612-35-3.mol

Synonyms:104612-35-3;(S)-(-)-2-Hydroxy-N-methylsuccinimide;(S)-3-hydroxy-1-methylpyrrolidine-2,5-dione;(S)-N-Methylhydroxysuccinimide;(3S)-3-HYDROXY-1-METHYLPYRROLIDINE-2,5-DIONE;(S)-3-Hydroxy-1-methyl-2,5-pyrrolidinedione;(S)-(-)-3-Hydroxy-1-methyl-2,5-pyrrolidinedione;SCHEMBL7955137;NLKACWKSCREJEL-VKHMYHEASA-N;DTXSID601306198;AMY30562;MFCD00221501;AKOS017343482;CS-0258606;(S)-(-)-2-Hydroxy-N-methylsuccinimide, 97%;EN300-7060523;A852367;J-001204

Chemical Property of (S)-(-)-2-Hydroxy-N-methylsuccinimide

Chemical Property:

• Vapor Pressure: 3.87E-05mmHg at 25°C
• Melting Point: 82-87 °C(lit.)
• Refractive Index: 1.549
• Boiling Point: 314.9°Cat760mmHg
• PKA: 11.25±0.20(Predicted)
• Flash Point: 144.3°C
• PSA: 57.61000
• Density: 1.438g/cm³
• LogP: -1.32610
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 129.042593085
• Heavy Atom Count: 9
• Complexity: 166

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-N-Methylhydroxysuccinimide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)CC(C1=O)O
• Isomeric SMILES: CN1C(=O)C[C@@H](C1=O)O
• Uses: (S)-(-)-2-Hydroxy-N-methylsuccinimide may be used as a chiral auxiliary to enhance the diastereomeric excess of the Diels-Alder adducts formed in asymmetric Diels-Alder reactions. A Hydroxysuccinimide derivative.

Technology Process of (S)-(-)-2-Hydroxy-N-methylsuccinimide

There total 5 articles about (S)-(-)-2-Hydroxy-N-methylsuccinimide 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: 98.0%

(S)-1-methyl-2,5-dioxopyrrolidin-3-yl acetate (171021-07-1) → (S)-3-hydroxy-1-methyl-2,5-pyrrolidinedione (104612-35-3)

Guidance literature:

With hydrogenchloride; ethanol;

DOI:10.1016/0040-4039(95)01648-2

Reference yield: 78.0%

(S)-Malic acid (97-67-6,78644-42-5) + methylamine (74-89-5) → (S)-3-hydroxy-1-methyl-2,5-pyrrolidinedione (104612-35-3)

Guidance literature:

In toluene; for 48h; Heating;

DOI:10.1021/jm00108a012

Reference yield:

malic acid (617-48-1,78644-42-5) + methylamine (74-89-5) → 3-hydroxy-N-methylsuccinimide (131237-81-5,104612-35-3,19948-27-7)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; water; at 15 ℃; for 14.5h; Solvent; Time; Reflux;

upstream raw materials:

malic acid

methylamine

(S)-Malic acid

(S)-1-methyl-2,5-dioxopyrrolidin-3-yl acetate

Downstream raw materials:

C₁₃H₁₇NO₄

1-methyl-3-pyrrolidinol

(3S)-1-methylpyrrolidin-3-yl (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate

((2S,3S,5S)-3-Benzyloxy-5-methoxycarbonylmethyl-1-methyl-pyrrolidin-2-yl)-acetic acid methyl ester

Refernces

• 1、 -. "SYNTHESIS OF AN ANTIVIRAL COMPOUND". Paragraph 0180; 0181. . Retrieved 2014/03/22.
• 2、 -. "Isothiazolecarboxylic acid derivatives and their use as microbicides". . . Retrieved 2008/06/13.