(S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester
• CAS No.: 681425-02-5
• Molecular Formula: C₂₀H₂₅F₂N₃O₄
• Molecular Weight: 409.433

Synonyms:(S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

Chemical Property of (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

There total 11 articles about (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl 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: 86.0%

(R)-(1α,5α,6α)-3-[4-(5-azidomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681425-03-6) → (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681425-02-5)

Guidance literature:

(R)-(1α,5α,6α)-3-[4-(5-azidomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester; With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 3h;

With water; In tetrahydrofuran; at 40 ℃; for 16h;

DOI:10.1021/jm058204j

Reference yield:

(1α,5α,6α)-3-benzyloxycarbonyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681424-87-3) → (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681425-02-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 0.423 g / H₂ / Pd(OH)2/C / methanol / 1.5 h

2.1: 92 percent / diisopropylethylamine / dimethylformamide / 20 h / 50 °C

3.1: Fe; aq. NH₄Cl / ethanol / 1.5 h / Heating

4.1: 0.71 g / pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: lithium hexamethyldisilylamide / tetrahydrofuran / 1.5 h / -78 °C

5.2: 87 percent / tetrahydrofuran / 16 h / 20 °C

6.1: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7.1: NaN₃ / dimethylformamide / 15 h / 70 °C

8.1: PPh₃ / tetrahydrofuran / 3 h / 20 °C

8.2: 86 percent / H₂O / tetrahydrofuran / 16 h / 40 °C

With pyridine; sodium azide; hydrogen; iron; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm058204j

Reference yield:

t-butyl diazoacetate (35059-50-8) → (S)-(1α,5α,6α)-3-[4-(5-aminomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester (681425-02-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Rh₂(OAc)4 / CH₂Cl₂

2.1: 0.423 g / H₂ / Pd(OH)2/C / methanol / 1.5 h

3.1: 92 percent / diisopropylethylamine / dimethylformamide / 20 h / 50 °C

4.1: Fe; aq. NH₄Cl / ethanol / 1.5 h / Heating

5.1: 0.71 g / pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: lithium hexamethyldisilylamide / tetrahydrofuran / 1.5 h / -78 °C

6.2: 87 percent / tetrahydrofuran / 16 h / 20 °C

7.1: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8.1: NaN₃ / dimethylformamide / 15 h / 70 °C

9.1: PPh₃ / tetrahydrofuran / 3 h / 20 °C

9.2: 86 percent / H₂O / tetrahydrofuran / 16 h / 40 °C

With pyridine; dirhodium tetraacetate; sodium azide; hydrogen; iron; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm058204j

upstream raw materials:

(R)-(1α,5α,6α)-3-[4-(5-azidomethyl-2-oxooxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

(1α,5α,6α)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

(1α,5α,6α)-3-benzyloxycarbonyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

Downstream raw materials:

exo-(1R,5S)-3-[4-((5S)-5-{[(dichloroacetyl)amino]methyl}-2-oxo-1,3-oxazolidin-3-yl)-2,6-difluorophenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

(S)-(1α,5α,6α)-3-(4-{5-[(2,2,-dichloroacetylamino)methyl]-2-oxooxazolidin-3-yl}-2,6-difluorophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

(S)-(1α,5α,6α)-3-(4-{5-[(2,2,-difluoroacetylamino)methyl]-2-oxooxazolidin-3-yl}-2,6-difluorophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

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