(5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

Base Information

• Chemical Name: (5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid
• CAS No.: 88140-14-1
• Molecular Formula: C₁₆H₁₈N₂O₄
• Molecular Weight: 302.33

Synonyms:(5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

Chemical Property of (5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

Chemical Property:

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Technology Process of (5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

There total 10 articles about (5R^*,6S^*)-2-(4'-aminomethylphenyl)-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid 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:

o-nitrobenzyl-(5R*,6S*)-2-(4'-azidomethylphenyl)-6-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate → (5R*,6S*)-2-(4'-aminomethylphenyl)-6-<(R*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid (88140-14-1)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; In 1,4-dioxane; ethanol; water; for 0.333333h; under 2068.6 Torr;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran (17100-68-4) → (5R*,6S*)-2-(4'-aminomethylphenyl)-6-<(R*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid (88140-14-1)

Guidance literature:

Multi-step reaction with 6 steps

2: 78 percent / 10percent H₂SO₄ aq. / acetic acid / 0.5 h / Ambient temperature

3: 72.4 percent / Et₃N / CH₂Cl₂ / 0 deg C, 0.5 h, RT, overnight

4: 1) lithium azide, LiBr / 1) DMF, RT, 0.5 h, 2) RT, 2 h

5: 58.4 percent / xylene / 1.5 h / Heating

6: 0.001N HCl / 10percent Pd/C / H₂O; dioxane; ethanol / 0.33 h / 2068.6 Torr

With hydrogenchloride; lithium azide; sulfuric acid; triethylamine; lithium bromide; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; xylene;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

4-bromobenzenemethanol (873-75-6) → (5R*,6S*)-2-(4'-aminomethylphenyl)-6-<(R*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid (88140-14-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / p-TsOH / CH₂Cl₂ / 2 h / Ambient temperature

3: 78 percent / 10percent H₂SO₄ aq. / acetic acid / 0.5 h / Ambient temperature

4: 72.4 percent / Et₃N / CH₂Cl₂ / 0 deg C, 0.5 h, RT, overnight

5: 1) lithium azide, LiBr / 1) DMF, RT, 0.5 h, 2) RT, 2 h

6: 58.4 percent / xylene / 1.5 h / Heating

7: 0.001N HCl / 10percent Pd/C / H₂O; dioxane; ethanol / 0.33 h / 2068.6 Torr

With hydrogenchloride; lithium azide; sulfuric acid; toluene-4-sulfonic acid; triethylamine; lithium bromide; palladium on activated charcoal; In 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; xylene;

DOI:10.1016/S0040-4020(01)92147-7

upstream raw materials:

2-((4-bromobenzyl)oxy)tetrahydro-2H-pyran

4-bromobenzenemethanol

{(2R,3S)-2-(2-Hydroxy-ethyl)-3-[(R)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-nitro-benzyl ester

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-hydroxymethylphenylcarbonyl)methyl-azetidin-2-one

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