(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester

Base Information

• Chemical Name: (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester
• CAS No.: 141047-67-8
• Molecular Formula: C₂₄H₃₈N₂O₅
• Molecular Weight: 434.576

Synonyms:(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester

Chemical Property of (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester

There total 7 articles about (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl 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:

4-HYDROXYPIPERIDINE (5382-16-1) → (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester (141047-67-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 16 h / Ambient temperature

2: diisopropylethylamine (DIEA) / CH₂Cl₂ / 26 h / Ambient temperature

3: KOH / H₂O / 24 h / Heating

4: 1.) 1-hydroxybenztriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -20 deg C, 2.) DMF, from -20 deg C to RT, overnight

5: H₂ / 20percent Pd/C / methanol / 64 h / 3040 Torr

6: (NH₄)2CO₃ / H₂O; nitromethane / 72 h / 48 °C

With potassium hydroxide; hydrogen; ammonium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; nitromethane; dichloromethane; water;

DOI:10.1021/jm00088a006

Reference yield:

N-Cbz-L-Phe (1161-13-3) → (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester (141047-67-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-hydroxybenztriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -20 deg C, 2.) DMF, from -20 deg C to RT, overnight

2: H₂ / 20percent Pd/C / methanol / 64 h / 3040 Torr

3: (NH₄)2CO₃ / H₂O; nitromethane / 72 h / 48 °C

With hydrogen; ammonium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; nitromethane; water;

DOI:10.1021/jm00088a006

Reference yield:

4-(Methoxymethoxy)-piperidine (130316-85-7) → (S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoic acid ethyl ester (141047-67-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 1-hydroxybenztriazole hydrate (HOBT), 2.) 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / 1.) DMF, -20 deg C, 2.) DMF, from -20 deg C to RT, overnight

2: H₂ / 20percent Pd/C / methanol / 64 h / 3040 Torr

3: (NH₄)2CO₃ / H₂O; nitromethane / 72 h / 48 °C

With hydrogen; ammonium carbonate; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; nitromethane; water;

DOI:10.1021/jm00088a006

upstream raw materials:

ethyl (2R)-2-bromohexanoate

4-(1,3-dioxabutyl)piperidine amide of L-phenylalanine

4-HYDROXYPIPERIDINE

N-Cbz-L-Phe

Downstream raw materials:

(2S,4S)-3-aza-2-butyl-4-<<4-(1,3-dioxabutyl)piperidin-1-yl>carbonyl>-5-phenylpentanamide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(2S,4S)-3-aza-2-butyl-4-<<4-(1,3-dioxabutyl)piperidin-1-yl>carbonyl>-5-phenylpentanamide of (2S,3S,5S)-2-amino-1-cyclohexyl-3-hydroxy-5-(n-butylcarbamoyl)-6-methylheptane

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

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