(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

Base Information

Chemical Name:(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride
CAS No.:1377615-50-3
Molecular Formula:C₁₈H₁₉FN₄O₄S₂*ClH
Molecular Weight:474.965
Hs Code.:

(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

Synonyms:(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

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Chemical Property of (1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

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Technology Process of (1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

There total 8 articles about (1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride 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: 100.0%

: 1377615-90-1
di-tert-butyl (1R,2R,3R,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(4-fluoro-3-methyl-phenyl)sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate

: 1377615-50-3
(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; at 70 ℃; for 2h;
DOI:10.1021/acs.jmedchem.6b01119

Reference yield: 93.0%

: 1377615-50-3
(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

Guidance literature:

Reference yield:

: 635318-04-6
(1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

: 1377615-50-3
(1R,2R,3R,4S,5R,6R)-2-amino-3-[(4-fluoro-3-methyl-phenyl)-sulfanylmethyl]-4-(1H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]-hexane-2,6-dicarboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 7 steps

1: toluene / 1 h / 80 °C

2: triethylamine; diisobutylaluminium hydride / toluene; tetrahydrofuran / 3 h / -78 °C

3: triethylamine / diethyl ether / 0.25 h / Heating; Inert atmosphere

4: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; diethyl ether / 6 h / Cooling

5: 19 h / 0 - 20 °C / Heating

6: caesium carbonate; sodium tris(acetoxy)borohydride / N,N-dimethyl-formamide / 72 h / Heating

7: hydrogenchloride / 1,4-dioxane / 2 h / 70 °C

With hydrogenchloride; dimethylsulfide borane complex; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; caesium carbonate; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide; toluene; 3: |Michael Addition;
DOI:10.1021/acs.jmedchem.6b01119