(2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide

Base Information

• Chemical Name: (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide
• CAS No.: 140660-95-3
• Molecular Formula: C₄₃H₇₄N₄O₇
• Molecular Weight: 759.083

Synonyms:

Chemical Property of (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide

There total 4 articles about (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide 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:

2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanoic acid (129921-93-3) → (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide (140660-95-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-hydroxybenzotriazole hydrate (HOBT), N-methylmorpholine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) / 1 a.) DMF, from -20 deg C to 0 deg C, 1 h, b.) 0 deg C, 24 h, 2 a.) DMF, 0 deg C, 4 h, b.) from 0 deg C to RT, 20 h

2: TFA / 1.) CH₂Cl₂, from -10 deg C to 0 deg C, 4 h,2.) THF, water, RT, 18 h

3: HOBT, N-methylmorpholine, EDC / dimethylformamide / 24 h / Ambient temperature

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00088a007

Reference yield:

(4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (140660-89-5) → (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide (140660-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 1.) CH₂Cl₂, from -10 deg C to 0 deg C, 4 h,2.) THF, water, RT, 18 h

2: HOBT, N-methylmorpholine, EDC / dimethylformamide / 24 h / Ambient temperature

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00088a007

Reference yield:

N,N,N'-trimethylpropane-1,3-diamine (4543-96-8) → (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethoxy]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid (3-dimethylamino-propyl)-methyl-amide (140660-95-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-hydroxybenzotriazole hydrate (HOBT), N-methylmorpholine, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) / 1 a.) DMF, from -20 deg C to 0 deg C, 1 h, b.) 0 deg C, 24 h, 2 a.) DMF, 0 deg C, 4 h, b.) from 0 deg C to RT, 20 h

2: TFA / 1.) CH₂Cl₂, from -10 deg C to 0 deg C, 4 h,2.) THF, water, RT, 18 h

3: HOBT, N-methylmorpholine, EDC / dimethylformamide / 24 h / Ambient temperature

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jm00088a007

upstream raw materials:

(2S,4S)-3-oxa-2-butyl-4-<<4-(1,3-dioxabutyl)piperidin-1-yl>carbonyl>-5-phenylpentanoic acid

2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanoic acid

(4S,5S)-4-Cyclohexylmethyl-5-{(S)-2-[(3-dimethylamino-propyl)-methyl-carbamoyl]-3-methyl-butyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

N,N,N'-trimethylpropane-1,3-diamine

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