(3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone
• CAS No.: 101143-97-9
• Molecular Formula: C₁₆H₁₉NO₅
• Molecular Weight: 305.331

Synonyms:(3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone

Chemical Property of (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone

There total 13 articles about (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone 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: 77.0%

methyl (2R)-2-<(2S,3S)-3-<(S)-1-hydroxyethyl>-4-oxoazetidin-2-yl>propanoate (139404-32-3) + benzoic acid (65-85-0,8013-63-6) → (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone (101143-97-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 25 ℃; for 2.5h;

DOI:10.1002/(sici)1099-0690(200004)2000:8<1595::aid-ejoc1595>3.3.co;2-5

Reference yield:

methyl (2Z,4E)-3-amino-2-methyl-2,4-hexadienoate (279673-26-6) → (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone (101143-97-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: MS 4 Angstroem / CH₂Cl₂ / 2 h / reflux

2.1: 99 percent / NaCNBH₃; bromocresol; 2N HCl/MeOH / methanol; CH₂Cl₂ / 15 h / -90 °C

3.1: 28 percent / 5percent aq.NaHCO₃ / CH₂Cl₂ / 1 h

4.1: m-chloroperbenzoic acid / diethyl ether / 0.5 h / 25 °C

4.2: 70 percent / 2 N HCL / 0.25 h / 25 °C

5.1: 69 percent / 10percent NaClO₂/10percent NaH₂PO₄ aq.; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 25 °C

6.1: 99 percent / H₂ / 10percent Pd/C / methanol / 2.5 h

7.1: 73 percent / DCC / acetonitrile / 1.5 h / reflux

8.1: 77 percent / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 2.5 h / 0 - 25 °C

With hydrogenchloride; methanol; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; MS 4 Angstroem; 2-bromo-6-methylphenol; hydrogen; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; 10percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol; 1.1: Cycloaddition / 2.1: Reduction / 3.1: Acylation / 4.1: Oxidation / 4.2: Hydrolysis / 5.1: Oxidation / 6.1: Hydrogenolysis / 7.1: Cyclization / 8.1: Acylation;

DOI:10.1002/(sici)1099-0690(200004)2000:8<1595::aid-ejoc1595>3.3.co;2-5

Reference yield:

(2S,3S,3aS,4aS,5R,8S,8aR)-2,5,10,10-tetramethyl-octahydro-2H-5,8-methano-isoxazolo[3,2-b]benzoxazol-3-carbonitrile (279673-25-5) → (3S,4S)-3-[(1R)-benzoyloxyethyl]-4-[(1R)-methoxycarbonyl]ethyl-2-azetidinone (101143-97-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Zn powder / tetrahydrofuran / 1 h / reflux

1.2: 62 percent / 50percent aq. K₂CO₃ / tetrahydrofuran / 0.5 h / 25 °C

2.1: 99 percent / NaCNBH₃; bromocresol; 2N HCl/MeOH / methanol; CH₂Cl₂ / 15 h / -90 °C

3.1: 28 percent / 5percent aq.NaHCO₃ / CH₂Cl₂ / 1 h

4.1: m-chloroperbenzoic acid / diethyl ether / 0.5 h / 25 °C

4.2: 70 percent / 2 N HCL / 0.25 h / 25 °C

5.1: 69 percent / 10percent NaClO₂/10percent NaH₂PO₄ aq.; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.5 h / 25 °C

6.1: 99 percent / H₂ / 10percent Pd/C / methanol / 2.5 h

7.1: 73 percent / DCC / acetonitrile / 1.5 h / reflux

8.1: 77 percent / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 2.5 h / 0 - 25 °C

With hydrogenchloride; methanol; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; 2-bromo-6-methylphenol; hydrogen; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; zinc; 10percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; tert-butyl alcohol; 1.1: Addition / 1.2: Hydrolysis / 2.1: Reduction / 3.1: Acylation / 4.1: Oxidation / 4.2: Hydrolysis / 5.1: Oxidation / 6.1: Hydrogenolysis / 7.1: Cyclization / 8.1: Acylation;

DOI:10.1002/(sici)1099-0690(200004)2000:8<1595::aid-ejoc1595>3.3.co;2-5

upstream raw materials:

(E)-(1-methoxyprop-1-enyloxy)trimethylsilane

Benzoic acid (R)-1-((2S,3R)-2-acetoxy-4-oxo-azetidin-3-yl)-ethyl ester

Benzoic acid (R)-1-((2R,3S)-2-acetyl-4-oxo-azetidin-3-yl)-ethyl ester

Benzoic acid (R)-1-((3S,4R)-2-oxo-4-trimethylsilanylethynyl-azetidin-3-yl)-ethyl ester

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