[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 103127-87-3
• Molecular Formula: C₂₄H₄₂N₄O₆S
• Molecular Weight: 514.687

Synonyms:[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

There total 4 articles about [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic 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:

(2R,3S)-4-cyclohexyl-1-(isopropylsulfonyl)-2-hydroxybutane hydrochloride (103127-91-9) + N-(tert-butoxycarbonyl)-L-histidine (17791-52-5) → [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (103127-87-3)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at -23 - 20 ℃;

DOI:10.1021/jm00394a035

Reference yield:

(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane (107202-61-9) → [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (103127-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 59 percent / triethylamine / methanol / 2 h / Heating

2: 97 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h

3: HCl / ethanol / Ambient temperature

4: 1-hydroxybenzotriazole monohydrate (HOBt), N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / -23 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a035

Reference yield:

(2R,3S)-3-(t-Boc-amino)-4-cyclohexyl-1-(isopropylsulfonyl)-2-hydroxybutane (110206-09-2) → [(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (103127-87-3)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / ethanol / Ambient temperature

2: 1-hydroxybenzotriazole monohydrate (HOBt), N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / -23 - 20 °C

With 4-methyl-morpholine; hydrogenchloride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00394a035

upstream raw materials:

(2R,3S)-4-cyclohexyl-1-(isopropylsulfonyl)-2-hydroxybutane hydrochloride

N-(tert-butoxycarbonyl)-L-histidine

(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane

(2R,3S)-3-(t-Boc-amino)-4-cyclohexyl-1-(isopropylsulfonyl)-2-hydroxybutane

Downstream raw materials:

N-{(S)-1-[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-3,3-dimethyl-butyramide

(2R,3S)-3-<<(O-benzylthreoninyl)histidyl>amino>-4-cyclohexyl-2-hydroxy-1-1-(isopropylsulfonyl)butane

{(S)-1-[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

{(R)-1-[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(propane-2-sulfonyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

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