(1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-methyl-5-oxopyrrolidin-3(S)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester

Base Information

• Chemical Name: (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-methyl-5-oxopyrrolidin-3(S)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester
• CAS No.: 162599-64-6
• Molecular Formula: C₂₁H₃₀N₂O₇S
• Molecular Weight: 454.544
• Mol file: 162599-64-6.mol

Synonyms:

Chemical Property of (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-methyl-5-oxopyrrolidin-3(S)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-methyl-5-oxopyrrolidin-3(S)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester

There total 17 articles about (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[1-methyl-5-oxopyrrolidin-3(S)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid pivaloyloxymethyl ester 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: 93.7%

Chloromethyl pivalate (18997-19-8) + sodium (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(R)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate → pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(R)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate (162599-64-6)

Guidance literature:

In N,N-dimethyl acetamide; for 1h;

DOI:10.7164/antibiotics.52.900

Reference yield: 80.0%

Chloromethyl pivalate (18997-19-8) + sodium (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(S)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate → pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(S)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate (162599-64-6)

Guidance literature:

In N,N-dimethyl acetamide; for 1h;

DOI:10.7164/antibiotics.52.900

Reference yield:

(R)-4-hydroxy-1-methyl-2-oxopyrrolidine (252642-41-4,222856-39-5) → pivaloyloxymethyl (1R,5S,6S)-6-[(R)-1-hydroxyethyl]-1-methyl-2-[(S)-1-methyl-5-oxopyrrolidin-3-ylthio]-1-carbapen-2-em-3-carboxylate (162599-64-6)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / CH₂Cl₂

2: acetonitrile / Heating

3: sodium methoxide / methanol

4: 85 percent / N,N-diisopropylethylamine / acetonitrile

5: 80 percent / NaHCO₃; H₂ / Pd/C / H₂O; tetrahydrofuran / 2 h / 30 °C

6: 80 percent / N,N-dimethyl-acetamide / 1 h

With hydrogen; sodium methylate; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide; water; acetonitrile; 1: mesylation / 2: Substitution / 3: Hydrolysis / 4: Substitution / 5: Hydrogenolysis / 6: Alkylation;

DOI:10.7164/antibiotics.52.900

upstream raw materials:

Chloromethyl pivalate

(S)-4-hydroxy-1-methyl-2-oxopyrrolidine

(R)-3-mercapto-1-methyl-5-oxopyrrolidine

(S)-4-methanesulfonyloxy-1-methyl-2-oxopyrrolidine