(S)-N¹-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

Base Information

• Chemical Name: (S)-N¹-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide
• CAS No.: 161852-71-7
• Molecular Formula: C₃₂H₃₆N₆O₅
• Molecular Weight: 584.675

Synonyms:(S)-N¹-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

Chemical Property of (S)-N¹-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

Chemical Property:

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Technology Process of (S)-N¹-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

There total 9 articles about (S)-N¹-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide 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: 64.0%

N'-((2S,3S)-3-{(S)-3-Carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-2-hydroxy-4-phenyl-butyl)-N'-(4-methoxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester (161852-00-2) → (S)-N1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide (161852-71-7)

Guidance literature:

With formic acid; for 17h; Ambient temperature;

DOI:10.1021/jm960022p

Reference yield:

quinoline-2-carboxylic acid (93-10-7,1199266-78-8) → (S)-N1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide (161852-71-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) dicyclohexylcarbodiimide, 2.) 1-hydroxybenzotriazole hydrate / 1.) THF, 10 min, 2.) THF, 18 h

2: 88 percent / HCl(gas) / dioxane / 3 h / 45 °C

3: 67 percent / 4-methylmorpholine, N,N'-dicyclohexylcarbodiimide, 3-hydroxy-1,2,3-benzotriazin-4(3H)-one / tetrahydrofuran / 22 h / -10 - 20 °C

4: 64 percent / HCO₂H / 17 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; formic acid; 1-hydroxybenzotriazol-hydrate; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm960022p

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (S)-N1-{(1S,2S)-1-Benzyl-2-hydroxy-3-[N-(4-methoxy-benzyl)-hydrazino]-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide (161852-71-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / ethanol / 3 h / Heating

2: 73 percent / TsOH, NaBH₃CN / tetrahydrofuran / 4 h / Ambient temperature

3: 59 percent / ethanol / 16 h / 80 °C

4: 87 percent / 1 N aq. K₂CO₃ / methanol / 16 h / Heating

5: 67 percent / 4-methylmorpholine, N,N'-dicyclohexylcarbodiimide, 3-hydroxy-1,2,3-benzotriazin-4(3H)-one / tetrahydrofuran / 22 h / -10 - 20 °C

6: 64 percent / HCO₂H / 17 h / Ambient temperature

With 4-methyl-morpholine; formic acid; sodium cyanoborohydride; potassium carbonate; toluene-4-sulfonic acid; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jm960022p

upstream raw materials:

N'-((2S,3S)-3-{(S)-3-Carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-2-hydroxy-4-phenyl-butyl)-N'-(4-methoxy-benzyl)-hydrazinecarboxylic acid tert-butyl ester

quinoline-2-carboxylic acid

4-methoxy-benzaldehyde

N-1-(tert-butoxycarbonyl)-N-2-<(4-methoxyphenyl)methyl>hydrazine

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