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

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Chemical Name:[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(propane-2-sulfonyl)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester
CAS No.:109865-03-4
Molecular Formula:C₂₅H₄₄N₄O₆S
Molecular Weight:528.714
Hs Code.:

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

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

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

There total 7 articles about [(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(propane-2-sulfonyl)-butylcarbamoyl]-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: 73.0%

: 109864-89-3
(2S,3S)-2-amino-1-cyclohexyl-3-hydroxy-5-(isopropylsulfonyl)pentane

: 17791-52-5
N-(tert-butoxycarbonyl)-L-histidine

: 109865-03-4
[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(propane-2-sulfonyl)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃; for 12h;
DOI:10.1021/jm00393a008

Reference yield:

: 98105-41-0
methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate

: 109865-03-4
[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(propane-2-sulfonyl)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / NaH / dimethylformamide / 3 h

2: 1.) 9-BBN, 2.)aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, RT, 5 h, 2.) THF, 65 deg C, 1 h

3: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

4: 86 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

5: 96 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / Ambient temperature

6: 82 percent / Ba(OH)2*8H₂O / dioxane; H₂O / 21 h / Heating

7: 73 percent / Et₃N, hydroxybenzotriazole (HOBT), DCC / dimethylformamide / 12 h / 25 °C

With barium dihydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; sodium hydride; benzotriazol-1-ol; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00393a008

Reference yield:

: 109864-83-7
(4S,5S)-4-(cyclohexylmethyl)-5-(2-hydroxyethyl)oxazolidin-2-one

: 109865-03-4
[(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(propane-2-sulfonyl)-butylcarbamoyl]-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

2: 86 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

3: 96 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: 82 percent / Ba(OH)2*8H₂O / dioxane; H₂O / 21 h / Heating

5: 73 percent / Et₃N, hydroxybenzotriazole (HOBT), DCC / dimethylformamide / 12 h / 25 °C

With barium dihydroxide; sodium hydride; benzotriazol-1-ol; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00393a008