N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

Base Information

Chemical Name:N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide
CAS No.:260353-92-2
Molecular Formula:C₁₉H₂₀FN₃O₃S₂
Molecular Weight:421.517
Hs Code.:

Synonyms:N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

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Chemical Property of N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

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Technology Process of N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

There total 20 articles about N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide 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: 46.0%

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: (1RS,2SR,5RS,6SR)-2-spiro-5'-hydantoin-6-fluoro-4,4-ethylenedithiobicyclo[3.1.0]hexane-6-carboxylic acid

: 260353-92-2
N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

: 321903-38-2
N-(R)-1-phenylethyl-(1S,2R,5S,6R)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 18h;
DOI:10.1021/jm000346k

Reference yield:

: ethyl (1RS,5RS,6RS)-6-fluoro-2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylate

: 260353-92-2
N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / 70percent aq. t-BuOOH; BnNMe₃OH / toluene; ethanol / 4 h / 20 °C

2: 76 percent / (PhSe)2; NaBH₄; AcOH / ethanol / 2.5 h / 35 °C

3: 86 percent / imidazole / dimethylformamide / 16 h

4: 99 percent / BF₃*OEt₂ / CHCl₃ / 16 h / 20 °C

5: 85 percent / DCC; DMSO; pyridine / TFA / 16 h / 20 °C

6: 1N aq. NaOH / ethanol

7: ethanol; H₂O / 8.5 h / 35 °C

8: 46 percent / EDC*HCl; HOBt*H₂O / dimethylformamide / 18 h

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; diphenyl diselenide; boron trifluoride diethyl etherate; N-benzyl-trimethylammonium hydroxide; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm000346k

Reference yield:

: ethyl (1R,3R,4R,5S,6R)-3,4-epoxy-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate

: 260353-92-2
N-(R)-1-phenylethyl-(1R,2S,5R,6S)-2-spiro-5'-hydantoin-4,4-ethylenedithio-6-fluorobicyclo[3.1.0]hexane-6-carboxylamide

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / (PhSe)2; NaBH₄; AcOH / ethanol / 2.5 h / 35 °C

2: 100 percent / imidazole / dimethylformamide / 16 h

3: 94 percent / BF₃*OEt₂ / CHCl₃ / 16 h / 20 °C

4: 76 percent / DCC; DMSO; pyridine / TFA / 16 h / 20 °C

5: 1N aq. NaOH / ethanol

6: ethanol; H₂O / 120 h / 35 °C

7: EDC*HCl; HOBt*H₂O / dimethylformamide / 13 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; diphenyl diselenide; boron trifluoride diethyl etherate; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In ethanol; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jm000346k