(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

Base Information

Chemical Name:(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid
CAS No.:75486-55-4
Molecular Formula:C₁₇H₂₀N₂O₄
Molecular Weight:316.357
Hs Code.:

Synonyms:(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

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Chemical Property of (1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

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Technology Process of (1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

There total 13 articles about (1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-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: 72.0%

: potassium (1R,5R,6S)-2-<4'-(azidomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

: 75486-55-4
(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

Guidance literature:: With 4-morpholinepropanesulfonic acid buffer; hydrogen; palladium on activated charcoal; In water; for 0.25h; under 2327.2 Torr; Ambient temperature;
DOI:10.1021/jm00388a022

Reference yield:

: 93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

: 75486-55-4
(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

Guidance literature:: Multi-step reaction with 13 steps

1: 73 percent / imidazole / dimethylformamide / 4 h / 47 °C

2: toluene / 12 h / Heating

3: 6.2 g / thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

4: 13.9 g / dimethylformamide / 1.5 h / Ambient temperature

5: triethylamine / CH₂Cl₂ / 1 h / 0 °C

6: 68 percent / tetrahydrofuran / 1 h / 0 °C

7: 79 percent / glacial acetic acid, tetra n-butylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature

8: 96 percent / triethylamine / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

9: 85 percent / LiN₃ / dimethylformamide / 2 h / Ambient temperature

10: 71 percent / xylene / 6 h / 130 °C

11: 44 percent / glacial acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

12: 39 percent / triphenylphosphine, potassium 2-ethylhexanoate, tetrakis(triphenylphosphine)palladium / ethyl acetate; CH₂Cl₂ / 0.08 h

13: 72 percent / H₂, 4-morpholinepropanesulfonic acid buffer / 10percent Pd/C / H₂O / 0.25 h / 2327.2 Torr / Ambient temperature

With pyridine; 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; lithium azide; 4-morpholinepropanesulfonic acid buffer; tetrabutyl ammonium fluoride; hydrogen; potassium 2-ethylhexanoate; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; xylene;
DOI:10.1021/jm00388a022

Reference yield:

: 107514-91-0
(3S,4R)-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<(tert-butyldimethylsilyl)oxy>carbonyl>ethyl>azetidin-2-one

: 75486-55-4
(1R,5R,6S)-2-<4'-(aminomethyl)phenyl>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1: toluene / 12 h / Heating

2: 6.2 g / thionyl chloride, pyridine / tetrahydrofuran / 0.75 h / -40 - -20 °C

3: 13.9 g / dimethylformamide / 1.5 h / Ambient temperature

4: triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 68 percent / tetrahydrofuran / 1 h / 0 °C

6: 79 percent / glacial acetic acid, tetra n-butylammonium fluoride / tetrahydrofuran / 4.5 h / Ambient temperature

7: 96 percent / triethylamine / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

8: 85 percent / LiN₃ / dimethylformamide / 2 h / Ambient temperature

9: 71 percent / xylene / 6 h / 130 °C

10: 44 percent / glacial acetic acid, tetra-n-butylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

11: 39 percent / triphenylphosphine, potassium 2-ethylhexanoate, tetrakis(triphenylphosphine)palladium / ethyl acetate; CH₂Cl₂ / 0.08 h

12: 72 percent / H₂, 4-morpholinepropanesulfonic acid buffer / 10percent Pd/C / H₂O / 0.25 h / 2327.2 Torr / Ambient temperature

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; lithium azide; 4-morpholinepropanesulfonic acid buffer; tetrabutyl ammonium fluoride; hydrogen; potassium 2-ethylhexanoate; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; xylene;
DOI:10.1021/jm00388a022