3-(Methoxycarbonyl)-4-methylpentanoate

Base Information

• Chemical Name: 3-(Methoxycarbonyl)-4-methylpentanoate
• CAS No.: 208113-95-5
• Molecular Formula: C8H13O4-
• Molecular Weight: 174.197
• Hs Code.: 2918990090
• DSSTox Substance ID: DTXSID50943059
• Wikidata: Q82920085
• Mol file: 208113-95-5.mol

Synonyms:DTXSID50943059;3-(Methoxycarbonyl)-4-methylpentanoate

Chemical Property of 3-(Methoxycarbonyl)-4-methylpentanoate

Chemical Property:

• Refractive Index: 1.4630 (estimate)
• Boiling Point: 272.4°Cat760mmHg
• PKA: 4.41±0.19(Predicted)
• Flash Point: 104.3°C
• PSA: 63.60000
• Density: 1.092g/cm³
• LogP: 0.90630
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 173.08138389
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

98%min ^*data from raw suppliers

(S)-3-(Methoxycarbonyl)-4-methylpentanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC(=O)[O-])C(=O)OC
• Isomeric SMILES: CC(C)[C@H](CC(=O)[O-])C(=O)OC

Technology Process of 3-(Methoxycarbonyl)-4-methylpentanoate

There total 6 articles about 3-(Methoxycarbonyl)-4-methylpentanoate 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:

3-(methoxycarbonyl)-4-methylpent-3-enoic acid (130165-83-2) → (R)-3-(methoxycarbonyl)-4-methylpentanoic acid (220498-08-8) + (S)-3-(methoxycarbonyl)-4-methylpentanoic acid (208113-95-5)

Guidance literature:

With hydrogen; sodium methylate; <(S,S)-(Me-BPE)Rh(cod)>BF4; In methanol; at 20 ℃; under 4125.3 Torr; Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3773(19980803)37:13/14<1931::AID-ANIE1931>3.0.CO;2-3

Reference yield:

(R)-2-tert-Butoxycarbonyl-3-isopropyl-succinic acid 1-tert-butyl ester 4-methyl ester → (S)-3-(methoxycarbonyl)-4-methylpentanoic acid (208113-95-5)

Guidance literature:

With trifluoroacetic acid; In toluene; for 5h; Heating;

DOI:10.1021/jm970812e

Reference yield:

methyl (S)-2-hydroxy-3-methylbutanoate (24347-63-5) → (S)-3-(methoxycarbonyl)-4-methylpentanoic acid (208113-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.17 h

2: 1.) NaH / 1.) DMF, 0 deg C, 3 h, 2.) DMF, CH₂Cl₂, 0 deg C, 3 h

3: TFA / toluene / 5 h / Heating

With 2,6-dimethylpyridine; sodium hydride; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/jm970812e

upstream raw materials:

3-(methoxycarbonyl)-4-methylpent-3-enoic acid

methyl (S)-2-hydroxy-3-methylbutanoate

(R)-methyl 2-hydroxy-3-methylbutanoate

(R)-1-(methoxycarbonyl)-2-methylpropyl trifluoromethanesulfonate

Downstream raw materials:

(S)-3-Methyl-2-(2-morpholin-4-yl-2-oxo-ethyl)-butyric acid

C₂₁H₃₁NO₄

methyl (S)-4-(2-(4-(4-(6-chloro-benzo[d]thiazol-2-ylamino)phenyl)pyridin-2-yl)hydrazino)-2-isopropyl-4-oxo-butanoate

C₁₄H₂₅NO₃

Refernces

• 1、 Burk, Mark J.,Bienewald, Frank,Harris, Michael,Zanotti-Gerosa, Antonio. "Practical access to 2-alkylsuccinates through asymmetric catalytic hydrogenation of Stobbe-derived itaconates". . p. 1931 - 1933. Retrieved 2007/10/03.