(5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Base Information

• Chemical Name: (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
• CAS No.: 80903-27-1
• Molecular Formula: C₂₄H₂₈N₂O₁₁S
• Molecular Weight: 552.559

Synonyms:

Chemical Property of (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

There total 8 articles about (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl 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: 38.0%

(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate (124093-85-2) → (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (80903-27-1,124093-86-3) + (pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methyl-1β-oxoceph-3-em-4-carboxylate (124093-86-3)

Guidance literature:

With formic acid; dihydrogen peroxide; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1021/jm00163a048

Reference yield:

Chloromethyl pivalate (18997-19-8) → (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (80903-27-1,124093-86-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 12.6 percent / Et₃N, KHCO₃ / dimethylformamide / 21 h / Ambient temperature

2: 1.) tert-BuMgCl, 2.) / 1.) THF, ether, -78 deg C, 1 h, 2.) -78 deg C, 1 h

3: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

4: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

5: 50 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 0 °C

6: 23 percent / 80percent phosphoric acid, pyridine / dioxane / 20 h / Heating

7: 99 mg / 30percent H₂O₂, formic acid / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; dmap; formic acid; phosphoric acid; tert-butylmagnesium chloride; hydrogen; dihydrogen peroxide; potassium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a048

Reference yield:

6,6-dibromopenicillanic acid pivaloyloxymethyl ester (69388-93-8) → (5R,6R,7S)-3-Methyl-7-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-5,8-dioxo-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (80903-27-1,124093-86-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) tert-BuMgCl, 2.) / 1.) THF, ether, -78 deg C, 1 h, 2.) -78 deg C, 1 h

2: 70 percent / H₂ / 10percent Pd/C / H₂O; tetrahydrofuran / 1.5 h

3: 97 percent / diisopropylethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

4: 50 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / 0 °C

5: 23 percent / 80percent phosphoric acid, pyridine / dioxane / 20 h / Heating

6: 99 mg / 30percent H₂O₂, formic acid / CH₂Cl₂ / 48 h / Ambient temperature

With pyridine; dmap; formic acid; phosphoric acid; tert-butylmagnesium chloride; hydrogen; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/jm00163a048

upstream raw materials:

(pivaloyloxy)methyl 7α-<1(R)-<<<(p-nitrobenzyl)oxy>carbonyl>oxy>ethyl>-3-methylceph-3-em-4-carboxylate

Chloromethyl pivalate

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

6,6-dibromopenicillanic acid pivaloyloxymethyl ester

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