4-Thiazolidinecarbonyl chloride, 3-[(4-methoxyphenyl)methyl]-2-oxo-, (4S)-

Base Information

• Chemical Name: 4-Thiazolidinecarbonyl chloride, 3-[(4-methoxyphenyl)methyl]-2-oxo-, (4S)-
• CAS No.: 646994-31-2
• Molecular Formula: C12H12ClNO3S
• Molecular Weight: 285.751
• Mol file: 646994-31-2.mol

Synonyms:

Chemical Property of 4-Thiazolidinecarbonyl chloride, 3-[(4-methoxyphenyl)methyl]-2-oxo-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Thiazolidinecarbonyl chloride, 3-[(4-methoxyphenyl)methyl]-2-oxo-, (4S)-

There total 6 articles about 4-Thiazolidinecarbonyl chloride, 3-[(4-methoxyphenyl)methyl]-2-oxo-, (4S)- 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-(4-methoxybenzyl)-2-oxo-thiazolidine-4-carboxylic acid (139944-38-0) → (S)-3-(4-Methoxy-benzyl)-2-oxo-thiazolidine-4-carbonyl chloride (646994-31-2)

Guidance literature:

With oxalyl dichloride; sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 6 h, 2.) THF, a) 0 deg C, 30 min, b) RT, 14 h;

DOI:10.1021/ja00034a036

Reference yield:

(-)-3-(4-methoxybenzyl)-2-oxo-thiazolidine-4-carboxylic acid ethyl ester (101860-50-8) → (S)-3-(4-Methoxy-benzyl)-2-oxo-thiazolidine-4-carbonyl chloride (646994-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / aq. KOH / dioxane / 1 h

2: 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine / tetrahydrofuran / 40 h / -18 °C

With potassium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1002/chem.200601135

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (S)-3-(4-Methoxy-benzyl)-2-oxo-thiazolidine-4-carbonyl chloride (646994-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / NaH / tetrahydrofuran

2: 98 percent / KOH / H₂O; diethyl ether

3: 1-chloro-2,N,N-trimethylprop-1-en-1-ylamine / tetrahydrofuran / -18 °C

With potassium hydroxide; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; sodium hydride; In tetrahydrofuran; diethyl ether; water;

DOI:10.1002/anie.200352413

upstream raw materials:

(-)-3-(4-methoxybenzyl)-2-oxo-thiazolidine-4-carboxylic acid

p-Methoxybenzyl bromide

(-)-3-(4-methoxybenzyl)-2-oxo-thiazolidine-4-carboxylic acid ethyl ester

p-methoxybenzyl chloride

Downstream raw materials:

(2Z,6E)-3-Methyl-deca-2,6-dien-8-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester

4-[2,4-dihydroxy-6-(3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

4-[2,4-dihydroxy-6-(3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one

6,7-(Z)-N-PMB-15-OMe-Latrunculin B

Refernces

• 1、 Fuerstner, Alois,De Souza, Dominic,Parra-Rapado, Liliana,Jensen, Jon T.. "Catalysis-Based Total Synthesis of Latrunculin B". . p. 5358 - 5360. Retrieved 2007/10/03.