(+/-)-<1R,S<1α,3(S^*,R^*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester

Base Information

• Chemical Name: (+/-)-<1R,S<1α,3(S^*,R^*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester
• CAS No.: 120566-75-8
• Molecular Formula: C₁₈H₂₀N₂O₆
• Molecular Weight: 360.367

Synonyms:

Chemical Property of (+/-)-<1R,S<1α,3(S^*,R^*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-<1R,S<1α,3(S^*,R^*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester

There total 5 articles about (+/-)-<1R,S<1α,3(S^*,R^*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid 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: 73.0%

(+/-)-6-Methyl-2,4-dioxo-α-phenyl-3,6-diazabicyclo<3.1.0>hexane-3-acetic acid methyl ester (120566-71-4,127420-40-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (+/-)-<1R,S<1α,3(S*,R*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester (120566-75-8,120566-76-9,120662-99-9,120663-00-5,135557-54-9,135557-55-0)

Guidance literature:

In 1,4-dioxane; for 8h;

DOI:10.1021/jo00020a035

Reference yield:

(S)-Phenylglycine methyl ester (6591-61-3,24461-61-8,26682-99-5,37760-98-8) → (+/-)-<1R,S<1α,3(S*,R*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester (120566-75-8,120566-76-9,120662-99-9,120663-00-5,135557-54-9,135557-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / diethyl ether / 20 h / Ambient temperature

2: 1.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / 1.) CH₂Cl₂ or THF, r.t., 20 h, 2.) toluene, 100 deg C, 18 h

3: 91 percent / toluene / 24 h / Ambient temperature

4: 82 percent / dioxane / 5 h / Irradiation

5: 73 percent / dioxane / 8 h

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; diethyl ether; toluene;

DOI:10.1021/jo00020a035

Reference yield:

-4-<<(Methoxycarbonyl)phenylmethyl>amino>-4-oxo-2-butenoic acid (120566-65-6) → (+/-)-<1R,S<1α,3(S*,R*),5α,6α>>-3-<(Methoxycarbonyl)phenylmethyl>-8-methyl-2,4-dioxo-3,8-diazabicyclo<3.2.1>octane-6-carboxylic acid methyl ester (120566-75-8,120566-76-9,120662-99-9,120663-00-5,135557-54-9,135557-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / 1.) CH₂Cl₂ or THF, r.t., 20 h, 2.) toluene, 100 deg C, 18 h

2: 91 percent / toluene / 24 h / Ambient temperature

3: 82 percent / dioxane / 5 h / Irradiation

4: 73 percent / dioxane / 8 h

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; toluene;

DOI:10.1021/jo00020a035

upstream raw materials:

(+/-)-6-Methyl-2,4-dioxo-α-phenyl-3,6-diazabicyclo<3.1.0>hexane-3-acetic acid methyl ester

acrylic acid methyl ester

(S)-Phenylglycine methyl ester

(+/-)-α-Phenyl-2,5-dioxo-1H-pyrrole-1-acetic acid methyl ester

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