(S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

Base Information

• Chemical Name: (S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide
• CAS No.: 180463-03-0
• Molecular Formula: C₃₆H₄₉N₇O₅
• Molecular Weight: 659.829

Synonyms:(S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

Chemical Property of (S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide

There total 13 articles about (S)-N¹-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-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: 100.0%

{(S)-1-[N'-((2S,3S)-3-{(S)-3-Carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-2-hydroxy-4-phenyl-butyl)-N'-cyclohexylmethyl-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid tert-butyl ester (180463-04-1) → (S)-N1-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide (180463-03-0)

Guidance literature:

With formic acid; for 22h; Ambient temperature;

DOI:10.1021/jm960022p

Reference yield:

(E)-tert-butyl 2-(cyclohexylmethylene)hydrazinecarboxylate (929016-50-2) → (S)-N1-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide (180463-03-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / H₂ / 5percent Pt/C / methanol / 8 h / 760 Torr / Ambient temperature

2: 61 percent / methanol / 16 h / Heating

3: 95 percent / 1 N aq. K₂CO₃ / methanol / 16 h / Heating

4: 76 percent / 4-methylmorpholine, N,N'-dicyclohexylcarbodiimide, 3-hydroxy-1,2,3-benzotriazin-4(3H)-one / tetrahydrofuran / 22 h / -10 - 20 °C

5: 100 percent / HCO₂H / 17 h / Ambient temperature

6: 52 percent / 4-methylmorpholine, O-benzotriazol-1-yl-N,N,N',N'-tetramethyluroniumhexafluorophosphate / acetonitrile / 17 h

7: 100 percent / HCO₂H / 22 h / Ambient temperature

With 4-methyl-morpholine; formic acid; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; dicyclohexyl-carbodiimide; platinum on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jm960022p

Reference yield:

cyclohexanecarbaldehyde (2043-61-0) → (S)-N1-{(1S,2S)-3-[N'-((S)-2-Amino-3-methyl-butyryl)-N-cyclohexylmethyl-hydrazino]-1-benzyl-2-hydroxy-propyl}-2-[(quinoline-2-carbonyl)-amino]-succinamide (180463-03-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / ethanol / 3 h / Heating

2: 95 percent / H₂ / 5percent Pt/C / methanol / 8 h / 760 Torr / Ambient temperature

3: 61 percent / methanol / 16 h / Heating

4: 95 percent / 1 N aq. K₂CO₃ / methanol / 16 h / Heating

5: 76 percent / 4-methylmorpholine, N,N'-dicyclohexylcarbodiimide, 3-hydroxy-1,2,3-benzotriazin-4(3H)-one / tetrahydrofuran / 22 h / -10 - 20 °C

6: 100 percent / HCO₂H / 17 h / Ambient temperature

7: 52 percent / 4-methylmorpholine, O-benzotriazol-1-yl-N,N,N',N'-tetramethyluroniumhexafluorophosphate / acetonitrile / 17 h

8: 100 percent / HCO₂H / 22 h / Ambient temperature

With 4-methyl-morpholine; formic acid; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; dicyclohexyl-carbodiimide; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; acetonitrile;

DOI:10.1021/jm960022p

upstream raw materials:

{(S)-1-[N'-((2S,3S)-3-{(S)-3-Carbamoyl-2-[(quinoline-2-carbonyl)-amino]-propionylamino}-2-hydroxy-4-phenyl-butyl)-N'-cyclohexylmethyl-hydrazinocarbonyl]-2-methyl-propyl}-carbamic acid tert-butyl ester

quinoline-2-carboxylic acid

t-Boc-L-valine

L-valine

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