Nalpha-[4-(4-aminopiperidin-1-yl)-2-benzyl-4-oxobutanoyl]-N-[(3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(pyridin-2-yl)hexan-2-yl]-L-histidinamide acetate (1:1)

Base Information

• Chemical Name: Nalpha-[4-(4-aminopiperidin-1-yl)-2-benzyl-4-oxobutanoyl]-N-[(3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(pyridin-2-yl)hexan-2-yl]-L-histidinamide acetate (1:1)
• CAS No.: 135683-92-0
• Molecular Formula: C₃₉H₅₅N₇O₅
• Molecular Weight: 701.91
• Mol file: 135683-92-0.mol

Synonyms:N--(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6(2-pyridyl)-hexane-2-amide acetate

Chemical Property of Nalpha-[4-(4-aminopiperidin-1-yl)-2-benzyl-4-oxobutanoyl]-N-[(3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(pyridin-2-yl)hexan-2-yl]-L-histidinamide acetate (1:1)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Nalpha-[4-(4-aminopiperidin-1-yl)-2-benzyl-4-oxobutanoyl]-N-[(3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(pyridin-2-yl)hexan-2-yl]-L-histidinamide acetate (1:1)

There total 16 articles about Nalpha-[4-(4-aminopiperidin-1-yl)-2-benzyl-4-oxobutanoyl]-N-[(3R,4S)-1-cyclohexyl-3,4-dihydroxy-6-(pyridin-2-yl)hexan-2-yl]-L-histidinamide acetate (1:1) 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:

(3R)-3-Benzyloxycarbonyl-3-phenylmethylpropionic acid (116129-80-7) → N--(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6(2-pyridyl)-hexane-2-amide acetate (135683-92-0)

Guidance literature:

Multi-step reaction with 6 steps

1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

2: Et₃N / CH₂Cl₂ / 3 h / 0 °C

3: 96.8 percent / H₂ / 10percent Pd/C / ethanol / 1.5 h / 760 Torr

4: 87.8 percent / HOBt*H₂O, N-ethylmorpholine, HBTU / acetonitrile / 2 h / Ambient temperature

5: 76.3 percent / thiophenol / acetonitrile / 2 h / Ambient temperature

6: trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With N-ethylmorpholine;; oxalyl dichloride; hydrogen; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; thiophenol; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00071a009

Reference yield:

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one (136159-65-4,96930-27-7) → N--(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6(2-pyridyl)-hexane-2-amide acetate (135683-92-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) sodium hexamethyldisilylamide / 1.) THF, -65 deg C, 45 min, 2.) THF, -70 deg C, 3 h

2: 1.) n-butyllithium / 1.) THF, hexane, -5 deg C, 2.) THF, hexane, 0 deg C, 3 h

3: 92.5 percent / trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

4: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

5: Et₃N / CH₂Cl₂ / 3 h / 0 °C

6: 96.8 percent / H₂ / 10percent Pd/C / ethanol / 1.5 h / 760 Torr

7: 87.8 percent / HOBt*H₂O, N-ethylmorpholine, HBTU / acetonitrile / 2 h / Ambient temperature

8: 76.3 percent / thiophenol / acetonitrile / 2 h / Ambient temperature

9: trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With N-ethylmorpholine;; n-butyllithium; oxalyl dichloride; hydrogen; sodium hexamethyldisilazane; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; thiophenol; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00071a009

Reference yield:

benzyl (2R)-2-<(tert-butyloxycarbonyl)methyl>-3-phenylpropionate (116129-88-5) → N--(2S,3R,4S)-1-cyclohexyl-3,4-dihydroxy-6(2-pyridyl)-hexane-2-amide acetate (135683-92-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 92.5 percent / trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

2: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

3: Et₃N / CH₂Cl₂ / 3 h / 0 °C

4: 96.8 percent / H₂ / 10percent Pd/C / ethanol / 1.5 h / 760 Torr

5: 87.8 percent / HOBt*H₂O, N-ethylmorpholine, HBTU / acetonitrile / 2 h / Ambient temperature

6: 76.3 percent / thiophenol / acetonitrile / 2 h / Ambient temperature

7: trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

With N-ethylmorpholine;; oxalyl dichloride; hydrogen; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; thiophenol; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00071a009

upstream raw materials:

(2S,3R,4S)-N-piperidyl>carbonyl>propionyl>-L-histidinyl>-1-cyclohexyl-3,4-dihydroxy-6-(2-pyridyl)hexan-2-amine

(3R)-3-Benzyloxycarbonyl-3-phenylmethylpropionic acid

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one

benzyl (2R)-2-<(tert-butyloxycarbonyl)methyl>-3-phenylpropionate

Refernces