1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

Base Information

Chemical Name:1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane
CAS No.:335161-00-7
Molecular Formula:C₂₆H₂₅ClFN₅O₄S
Molecular Weight:558.033
Hs Code.:

Synonyms:1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

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Chemical Property of 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

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Technology Process of 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

There total 12 articles about 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane 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: 55.0%

: 335160-95-7
3-(bromomethyl)-4-chloro-1-phenyl methanesulfonate

: 335160-97-9
1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

: 335161-00-7
1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

Guidance literature:: 1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

3-(bromomethyl)-4-chloro-1-phenyl methanesulfonate; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Further stages.;
DOI:10.1021/ol015504w

Reference yield:

: 5(S)-5-allyl-3-benzyl-4-tert-butoxycarbonyl-1-(2,4-dimethoxybenzyl)-2-piperazinone

: 335161-00-7
1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 8 steps

1.1: OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 2.5 h

1.2: NaIO₄; NaHCO₃ / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 2 h

2.1: 70 percent / NaBH₄ / ethanol / 0.33 h / 0 °C

3.1: 90 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: 63 percent / LDA / tetrahydrofuran / -78 - 0 °C

5.1: 100 percent / HCl / ethyl acetate / 0.38 h / 0 °C

6.1: 56 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 24 h

7.1: TfOH; Et₃SiH / CH₂Cl₂; acetonitrile / 336 h

8.1: NaH / dimethylformamide / 0.08 h / 20 °C

8.2: 55 percent / dimethylformamide / 1 h / 0 °C

With hydrogenchloride; triethylsilane; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ol015504w

Reference yield:

: (1S,5S)-1-Benzyl-3-(2,4-dimethoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one; hydrochloride

: 335161-00-7
1(R),5(S)-8-[1-(4-cyano-3-fluorobenzyl)-5-imidazolylmethyl]-3-[2-chloro-5-(methanesulfonyloxy)benzyl]-3,8-diaza-2-oxobicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 56 percent / Na(AcO)3BH; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 24 h

2.1: TfOH; Et₃SiH / CH₂Cl₂; acetonitrile / 336 h

3.1: NaH / dimethylformamide / 0.08 h / 20 °C

3.2: 55 percent / dimethylformamide / 1 h / 0 °C

With triethylsilane; trifluorormethanesulfonic acid; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydride; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol015504w