methyl [2alpha,3beta(R*)]-2-chloro-alpha-(isopropylidene)-4-oxo-3-[1-[[(2,2,2-trichloroethoxy)carbonyl]oxy]ethyl]azetidine-1-acetate

Base Information

• Chemical Name: methyl [2alpha,3beta(R*)]-2-chloro-alpha-(isopropylidene)-4-oxo-3-[1-[[(2,2,2-trichloroethoxy)carbonyl]oxy]ethyl]azetidine-1-acetate
• CAS No.: 76431-35-1
• Molecular Formula: C14H17 Cl4 N O6
• Molecular Weight: 437.104
• Mol file: 76431-35-1.mol

Synonyms:methyl [2alpha,3beta(R*)]-2-chloro-alpha-(isopropylidene)-4-oxo-3-[1-[[(2,2,2-trichloroethoxy)carbonyl]oxy]ethyl]azetidine-1-acetate

Chemical Property of methyl [2alpha,3beta(R*)]-2-chloro-alpha-(isopropylidene)-4-oxo-3-[1-[[(2,2,2-trichloroethoxy)carbonyl]oxy]ethyl]azetidine-1-acetate

Chemical Property:

• PSA: 82.14000
• LogP: 3.32640

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl [2alpha,3beta(R*)]-2-chloro-alpha-(isopropylidene)-4-oxo-3-[1-[[(2,2,2-trichloroethoxy)carbonyl]oxy]ethyl]azetidine-1-acetate

There total 5 articles about methyl [2alpha,3beta(R*)]-2-chloro-alpha-(isopropylidene)-4-oxo-3-[1-[[(2,2,2-trichloroethoxy)carbonyl]oxy]ethyl]azetidine-1-acetate 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:

(2S,5R,6S)-3,3-Dimethyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (76431-34-0) → methyl (2α,3β(R*))-2-chloro-α-(isopropylidene)-4-oxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate (76431-35-1)

Guidance literature:

With chlorine; In tetrachloromethane; at -20 ℃; Yield given;

DOI:10.1016/S0040-4039(01)81938-9

Reference yield:

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate (80629-46-5) → methyl (2α,3β(R*))-2-chloro-α-(isopropylidene)-4-oxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate (76431-35-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / hydrogen / 10percent Pd/CaCO₃

2: pyridine / CH₂Cl₂

3: Cl₂ / CCl₄ / -20 °C

With pyridine; hydrogen; chlorine; Lindlar's catalyst; In tetrachloromethane; dichloromethane;

DOI:10.1016/S0040-4039(01)81938-9

Reference yield:

6,6-dibromopenicillanic acid (24158-88-1) → methyl (2α,3β(R*))-2-chloro-α-(isopropylidene)-4-oxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate (76431-35-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / K₂CO₃ / dimethylformamide

2: 60 percent

3: 60 percent / hydrogen / 10percent Pd/CaCO₃

4: pyridine / CH₂Cl₂

5: Cl₂ / CCl₄ / -20 °C

With pyridine; hydrogen; chlorine; potassium carbonate; Lindlar's catalyst; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)81938-9

upstream raw materials:

(2S,5R,6S)-3,3-Dimethyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

methyl (3S,5R,6S)-6-<(R)-1-hydroxyethyl>penicillanate

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate

6,6-dibromopenicillanic acid

Downstream raw materials:

Carbonic acid (R)-1-((2R,3S)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester

{(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

methyl (2α,3β(R*))-2-chloro-α,4-dioxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate