sodium (+/-)-cis-6β-<(1S^*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: sodium (+/-)-cis-6β-<(1S^*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 98243-79-9
• Molecular Formula: C₁₅H₁₄NO₄S*Na
• Molecular Weight: 327.336

Synonyms:sodium (+/-)-cis-6β-<(1S^*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property of sodium (+/-)-cis-6β-<(1S^*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of sodium (+/-)-cis-6β-<(1S^*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 8 articles about sodium (+/-)-cis-6β-<(1S^*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 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: 68.2%

p-nitrobenzyl (+/-)-cis-6β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (78072-35-2,79299-26-6,92218-03-6) → sodium (+/-)-cis-6β-<(1S*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (98243-79-9)

Guidance literature:

With hydrogen; sodium hydrogencarbonate; platinum(IV) oxide; In tetrahydrofuran; for 0.666667h; Pressure (range begins): 40 ; Ambient temperature;

DOI:10.1039/P19810002282

Reference yield:

(+/-)-4β-carboxymethyl-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (76335-76-7,77448-00-1,79299-25-5,90581-13-8,150284-14-3) → sodium (+/-)-cis-6β-<(1S*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (98243-79-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NN'-carbonyldi-imidazole / 1.) THF, RT, 4 h, 2.) THF, RT, 12 h

2: 93 percent / toluene-p-sulphonyl azide, triethylamine / acetonitrile / 1.5 h / Ambient temperature

3: 92 percent / rhodium⁽¹¹⁾ acetate / benzene / 0.5 h / 80 °C

4: 1.) di-isopropylethylamine, diphenyl chlorophosphate, 2.) di-isopropylethylamine / 1.) acetonitrile, 0 deg C, 10 min, 2.) acetonitrile, 0 deg C, 1 h

5: 68.2 percent / 0.068M-aq. sodium hydrogencarbonate, hydrogen / Adams catalyst / tetrahydrofuran / 0.67 h / Ambient temperature

With rhodium(II) acetate; 4-toluenesulfonyl azide; hydrogen; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; platinum(IV) oxide; In tetrahydrofuran; acetonitrile; benzene;

DOI:10.1039/P19810002282

Reference yield:

cis-3-(1'R*-hydroxyethyl-4-(2',2'-dimethoxyethyl))-2-azetidinone (72447-85-9,72496-42-5,72843-53-9,72843-54-0,73890-29-6,73890-30-9,74164-94-6,74164-95-7,78088-39-8,79299-24-4,79952-68-4,81076-43-9) → sodium (+/-)-cis-6β-<(1S*)-1-hydroxyethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (98243-79-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 60 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / -5 - 0 °C

2: 79 percent / 80percent acetic acid / 4 h / 55 - 60 °C

3: 81 percent / 8N-Jones reagent / acetone

4: 1.) NN'-carbonyldi-imidazole / 1.) THF, RT, 4 h, 2.) THF, RT, 12 h

5: 93 percent / toluene-p-sulphonyl azide, triethylamine / acetonitrile / 1.5 h / Ambient temperature

6: 92 percent / rhodium⁽¹¹⁾ acetate / benzene / 0.5 h / 80 °C

7: 1.) di-isopropylethylamine, diphenyl chlorophosphate, 2.) di-isopropylethylamine / 1.) acetonitrile, 0 deg C, 10 min, 2.) acetonitrile, 0 deg C, 1 h

8: 68.2 percent / 0.068M-aq. sodium hydrogencarbonate, hydrogen / Adams catalyst / tetrahydrofuran / 0.67 h / Ambient temperature

With rhodium(II) acetate; dmap; 4-toluenesulfonyl azide; jones reagent; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1039/P19810002282

upstream raw materials:

p-nitrobenzyl (+/-)-cis-6β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-3-phenylthio-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(+/-)-4β-carboxymethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

cis-3-(1'R^*-hydroxyethyl-4-(2',2'-dimethoxyethyl))-2-azetidinone

(+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

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