938063-63-9

Basic information

• Product Name: 3-[(2,2-Dimethyl-1-oxobutyl)thio]propanoic acid methyl ester
• Synonyms: DIMETHYLBUTYRYL-S-METHYL MERCAPTOPROPIONATE (DMB-S-MMP);2-diMethylbutanoylthio)propanoate;Methyl 3-(2;α-DiMethylbutyryl-S-Methyl Mercaptopropionate;Alphatwo Methylisobutyryl-S-Methyl propionate;Methyl 3-((2,2-diMethylbutanoyl)thio)propanoate;3-[(2,2-Dimethyl-1-oxobutyl)thio]propanoic acid methyl ester
• CAS NO: 938063-63-9
• Molecular Formula: C₁₀H₁₈O₃S
• Molecular Weight: 218
• Mol File: 938063-63-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 281℃
• Flash Point: 119℃
• Appearance: /
• Density: 1.048
• Vapor Pressure: 0.495Pa at 25℃
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-[(2,2-Dimethyl-1-oxobutyl)thio]propanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2,2-Dimethyl-1-oxobutyl)thio]propanoic acid methyl ester(938063-63-9)
• EPA Substance Registry System: 3-[(2,2-Dimethyl-1-oxobutyl)thio]propanoic acid methyl ester(938063-63-9)

Safety Data

• Hazardous Substances Data: 938063-63-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1S/C10H18O3S/c1-5-10(2,3)9(12)14-7-6-8(11)13-4/h5-7H2,1-4H3

Synthetic route

Methyl 3-mercaptopropionate (2935-90-2) + 2,2-dimethylbutanoyl chloride (5856-77-9) → methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9)

Conditions	Yield
Stage #1: Methyl 3-mercaptopropionate; 2,2-dimethylbutanoyl chloride In dichloromethane at 10℃; for 0.25h; Stage #2: With ammonia In dichloromethane at 0 - 65℃; for 1.8h; pH=7; Time; Solvent;	98.4%
With N-ethyl-N,N-diisopropylamine In Isopropyl acetate at 2 - 25℃; for 2.16h;	80%
at 50℃; for 18h; Temperature;	79.5 g

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9) + monacolin J hydroxy acid (132748-10-8) → simvastatin acid (121009-77-6)

Conditions	Yield
Kinetics; Reagent/catalyst;

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9) + monacolin J hydroxy acid (132748-10-8) → simvastatin sodium salt (101314-97-0)

Conditions	Yield
Stage #1: monacolin J hydroxy acid With sodium hydroxide In water at 25℃; Stage #2: With hydrogenchloride; LovD acyltransferase; pyrographite In water at 25℃; for 0.0833333h; Enzymatic reaction; Stage #3: methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate In water at 25℃; Enzymatic reaction;

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9) + monacolin J hydroxy acid (132748-10-8) → simvastatin ammonium salt (139893-43-9)

Conditions	Yield
Stage #1: monacolin J hydroxy acid With ammonium hydroxide In water Stage #2: With hydrogenchloride; LovD acyltransferase In water at 25℃; for 0.0833333h; pH=9 - 9.2; Enzymatic reaction; Stage #3: methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate In water at 25℃; Enzymatic reaction;
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 25 °C 1.2: 3407 / 0.08 h / 25 °C / Enzymatic reaction 1.3: 3407 / 25 °C / Enzymatic reaction 2.1: ammonium hydroxide / ethyl acetate; methanol / 2.16 h / 0 - 22 °C View Scheme

methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate (938063-63-9) + C24H36O5 → C25H38O5*H3N

Conditions	Yield
Stage #1: C24H36O5 With potassium hydroxide In water; isopropyl alcohol at 72℃; for 5h; Inert atmosphere; Stage #2: methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate With hydrogenchloride; acyltransferase In water at 0.5℃; pH=9.5; Enzymatic reaction; Stage #3: With ammonium hydroxide In methanol at 7 - 15℃; for 2h; pH=7 - 8; Temperature; Reagent/catalyst; Solvent;

Upstream product

• 2935-90-2 Methyl 3-mercaptopropionate 
• 5856-77-9 2,2-dimethylbutanoyl chloride 

Downstream Products

• 101314-97-0 simvastatin sodium salt 
• 139893-43-9 simvastatin ammonium salt 
• 121009-77-6 simvastatin acid 

Relevant articles and documents

Method for green synthesis of simvastatin side chain (by machine translation)

The method, comprises the following steps, adding :(1) dimethyl butanoic acid 2,2 - thionyl chloride, to the reaction vessel in a pot method, to carry out the esterification reaction ;(2) to obtain the product (1) dimethyl - 1 1-oxobutyl 3 -methyl propionate, through a solventless method, thereby reducing the material cost 3 - [(2,2 - without using any acid-binding agent) in the esterification step] and reducing the pollution, to the environment by a one-pot, method, at the same time without using any acid-tie-acid-acid-tie-acid-acid methyl ester, to carry out esterification reaction in a solvent concentration step, in the, esterification step by using a solventless method in a step, in the esterification reaction step, to obtain the, product (dimethyl) chloride, in the esterification step. (by machine translation)

Lov-D acyltransferase mediated acylation

Methods for the improved acylation of chemical substrates using LovD acyltransferases, thioesters having acyl groups, and (i) thiol scavengers and/or (ii) precipitating agents are presented. An improved method for the production of simvastatin using (i) activated charcoal as a thiol scavenger and/or (ii) ammonium hydroxide as a precipitating agent is also presented.