1-Azadicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-[[2-(acethylamino)ethyl]thio]-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester

Base Information

• Chemical Name: 1-Azadicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-[[2-(acethylamino)ethyl]thio]-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester
• CAS No.: 84830-55-7
• Molecular Formula: C₂₀H₂₈N₂O₇S
• Molecular Weight: 440.518
• Mol file: 84830-55-7.mol

Synonyms:1-Azadicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-[[2-(acethylamino)ethyl]thio]-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester

Chemical Property of 1-Azadicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-[[2-(acethylamino)ethyl]thio]-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester

Chemical Property:

• Boiling Point: 707.4±60.0 °C(Predicted)
• PKA: 13.57±0.10(Predicted)
• PSA: 147.54000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 1.06020

Purity/Quality:

99.0%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Azadicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-[[2-(acethylamino)ethyl]thio]-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester

There total 9 articles about 1-Azadicyclo(3.2.0)hept-3-ene-2-carboxylic acid, 3-[[2-(acethylamino)ethyl]thio]-6-(2-hydroxy-1-methylethylidene)-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl 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: 16.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + pivaloyloxymethyl (5S*,6S*)-2-(2-acetamidoethyl)thio-6-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-1-em-3-carboxylate (109204-73-1) → pivaloyloxymethyl 2-(2-acetamidomethyl)thio-6-<(E)-1-(hydroxymethyl)ethylidene>carbapen-2-em-3-carboxylate (109204-75-3) + 3-(2-Acetylamino-ethylsulfanyl)-6-[2-hydroxy-1-methyl-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (84830-55-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; Yield given. Multistep reaction; 1.) CH₂Cl₂, 2 h, room temperature; 2.) 3 h, room temperature;

DOI:10.1248/cpb.33.4346

Reference yield:

(RS)-4-allyl-1-azetidin-2-one (74819-64-0) → 3-(2-Acetylamino-ethylsulfanyl)-6-[2-hydroxy-1-methyl-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (84830-55-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 51 percent / 1.) n-butyllithium, diisopropylamine; 2.) acetic acid / 1.) hexan/THF, -70 degC, 30 min; 2.) MeOH, room temperature

2: 95 percent / pyridine / toluene / 0.5 h

3: 96 percent / acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) triethylamine / 1.) DMF, room temperature; 2.) DMF, 2 h

5: 1.) ozone, trifluoroacetic acid, dimethylsulfide; 2.) NaHCO₃ / 1.) CH₂Cl₂, -60 degC, 1 h, room temperature; 2.) EtOAc/water, 1 h, room temperature

6: 83 percent / tetrahydrofuran; dimethylformamide / 0.25 h / Ambient temperature

7: m-chloroperbenzoic acid / CH₂Cl₂ / ice-cooling

8: 60 percent / thionyl chloride, pyridine / CH₂Cl₂ / 0.5 h

9: 1.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, 2 h, room temperature; 2.) 3 h, room temperature

With pyridine; n-butyllithium; thionyl chloride; dimethylsulfide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.33.4346

Reference yield:

(3S*,4R*)-4-allyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone (84829-82-3,84848-61-3,91926-19-1,91926-20-4) → 3-(2-Acetylamino-ethylsulfanyl)-6-[2-hydroxy-1-methyl-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (84830-55-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) triethylamine / 1.) DMF, room temperature; 2.) DMF, 2 h

2: 1.) ozone, trifluoroacetic acid, dimethylsulfide; 2.) NaHCO₃ / 1.) CH₂Cl₂, -60 degC, 1 h, room temperature; 2.) EtOAc/water, 1 h, room temperature

3: 83 percent / tetrahydrofuran; dimethylformamide / 0.25 h / Ambient temperature

4: m-chloroperbenzoic acid / CH₂Cl₂ / ice-cooling

5: 60 percent / thionyl chloride, pyridine / CH₂Cl₂ / 0.5 h

6: 1.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, 2 h, room temperature; 2.) 3 h, room temperature

With pyridine; thionyl chloride; dimethylsulfide; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.4346

upstream raw materials:

N,O-bis-(trimethylsilyl)-acetamide

pivaloyloxymethyl (5S^*,6S^*)-2-(2-acetamidoethyl)thio-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-1-em-3-carboxylate

(RS)-4-allyl-1-azetidin-2-one

(3S^*,4R^*)-4-allyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone