2-Methylserine

Base Information

• Chemical Name: 2-Methylserine
• CAS No.: 5424-29-3
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• Hs Code.: 29225000
• European Community (EC) Number: 226-565-5
• NSC Number: 163492,12135,11203
• UNII: CZ8HQ2F53F
• DSSTox Substance ID: DTXSID001346506
• Nikkaji Number: J80.719B
• Wikidata: Q27102625
• Metabolomics Workbench ID: 51047
• ChEMBL ID: CHEMBL539702
• Mol file: 5424-29-3.mol

Synonyms:2-methylserine;2-methylserine, (DL-Ser)-isomer;alpha-methylserine

Chemical Property of 2-Methylserine

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Melting Point: 253-263 °C
• Refractive Index: 1.513
• Boiling Point: 345.8 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 162.9 °C
• PSA: 83.55000
• Density: 1.317 g/cm³
• LogP: -0.51900
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, Heated), Water (Slightly
• XLogP3: -3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 119.058243149
• Heavy Atom Count: 8
• Complexity: 104

Purity/Quality:

99%, ^*data from raw suppliers

α-Methyl-D,L-serine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CO)(C(=O)O)N
• Uses: A useful synthetic intermediate A serine derivative. Alpha-Methyl-Dl-Serine is used in the synthesis of constrained amino acid buildings blocks and their incorporation into biologically active peptidomimetics. A serine derivative. Used in the synthesis of constrained amino acid buildings blocks and their incorporation into biologically active peptidomimetics.

Technology Process of 2-Methylserine

There total 52 articles about 2-Methylserine 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: 93.0%

(2R,4S)-methyl 2-tert-butyl-3-formyl-4-methyloxazolidine-4-carboxylate (93250-94-3) → (S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid (3398-40-1,5424-29-3,16820-18-1,81132-44-7)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 1.5h; freeing from salt with Dowex W₅₀*X₈;

DOI:10.1002/hlca.19870700426

Reference yield: 93.0%

((R)-1-Cyano-2-methoxymethoxy-1-methyl-ethyl)-carbamic acid methyl ester → (S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid (3398-40-1,5424-29-3,16820-18-1,81132-44-7)

Guidance literature:

With hydrogenchloride; for 12h; Heating;

DOI:10.1016/S0040-4020(98)00937-5

Reference yield: 92.0%

(1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.02,7]undec-2-en-5-one (1059607-17-8) → (S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid (3398-40-1,5424-29-3,16820-18-1,81132-44-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 90 ℃; for 4h;

DOI:10.1016/j.tetasy.2008.06.033

upstream raw materials:

(2S)-3-hydroxy-2-(N-benzyloxyamino)-2-methylpropionic acid

(1S,4S,7S,8R)-4,8,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one

5-hydroxymethyl-5-methyl-imidazolidine-2,4-dione

formaldehyd

Downstream raw materials:

formaldehyd

rac-Ala-OH

(R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester

3-(4-chloro-3-trifluoromethyl-phenyl)-5-hydroxymethyl-5-methyl-imidazolidine-2,4-dione

Refernces

• 1、 -. "Method for preparing 2-methylserine". Paragraph 0021; 0022; 0025; 0026; 0029; 0035. . Retrieved 2019/01/24.
• 2、 Wang, Hai-Fei,Ma, Guo-Hua,Yang, Shao-Bo,Han, Rong-Gang,Xu, Peng-Fei. "A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones". . p. 1630 - 1635. Retrieved 2008/12/21.