methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate

Base Information

• Chemical Name: methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate
• CAS No.: 95967-23-0
• Molecular Formula: C₁₅H₁₄N₂O₅
• Molecular Weight: 302.287
• Mol file: 95967-23-0.mol

Synonyms:methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate

Chemical Property of methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate

There total 1 articles about methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate 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: 63.0%

methyl 4-hydroxy-2-butynoate (31555-05-2) + (1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene (86823-92-9) → methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate (95967-23-0)

Guidance literature:

boron trifluoride diethyl etherate; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88797-4

Reference yield: 68.0%

thiophenol (108-98-5) + methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate (95967-23-0) → methyl E,Z-4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-3-phenylthio-2-butenoate (95967-26-3,96038-92-5)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88797-4

Reference yield:

methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-2-butynoate (95967-23-0) → methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-acetoacetate (95967-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / triethylamine / tetrahydrofuran / 3 h / Ambient temperature

2: 1.) N-bromoacetamide; 2.) Na₂SO₃ / 1.) dioxane, H₂O, 0 deg C

With triethylamine; sodium sulfite; N-bromoacetamide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)88797-4

upstream raw materials:

methyl 4-hydroxy-2-butynoate

(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-ene

Downstream raw materials:

methyl E,Z-4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-3-phenylthio-2-butenoate

methyl 4-<3(R)-benzoylamino-2-azetidinon-4(R)-yloxy>-acetoacetate