L-Histidinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-N-[1-(cyclohexylmethyl)- 2-hydroxy-3-[[2-oxo-2-[(1-oxido-1-azabicyclo[2.2.2]oct-3-yl)amino]ethyl] sulfonyl]propyl]-1-[(1,1-dimethylethoxy)carbonyl]-

Base Information

• Chemical Name: L-Histidinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-N-[1-(cyclohexylmethyl)- 2-hydroxy-3-[[2-oxo-2-[(1-oxido-1-azabicyclo[2.2.2]oct-3-yl)amino]ethyl] sulfonyl]propyl]-1-[(1,1-dimethylethoxy)carbonyl]-
• CAS No.: 142843-22-9
• Molecular Formula: C44H67N7O11S
• Molecular Weight: 902.122
• Mol file: 142843-22-9.mol

Synonyms:

Chemical Property of L-Histidinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-N-[1-(cyclohexylmethyl)- 2-hydroxy-3-[[2-oxo-2-[(1-oxido-1-azabicyclo[2.2.2]oct-3-yl)amino]ethyl] sulfonyl]propyl]-1-[(1,1-dimethylethoxy)carbonyl]-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Histidinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-N-[1-(cyclohexylmethyl)- 2-hydroxy-3-[[2-oxo-2-[(1-oxido-1-azabicyclo[2.2.2]oct-3-yl)amino]ethyl] sulfonyl]propyl]-1-[(1,1-dimethylethoxy)carbonyl]-

There total 6 articles about L-Histidinamide, N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl-N-[1-(cyclohexylmethyl)- 2-hydroxy-3-[[2-oxo-2-[(1-oxido-1-azabicyclo[2.2.2]oct-3-yl)amino]ethyl] sulfonyl]propyl]-1-[(1,1-dimethylethoxy)carbonyl]- 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: 40.0%

4-[(S)-2-{(1S,2R)-3-[(1-Aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methylsulfanyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester (142843-21-8) → 4-((S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-{(1S,2R)-1-cyclohexylmethyl-2-hydroxy-3-[(1-oxy-1-aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methanesulfonyl]-propylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid tert-butyl ester (142843-22-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1021/jm00093a009

Reference yield:

quinuclidin-3-amine (76883-48-2,120570-05-0,123536-15-2,6238-14-8,781591-76-2) → 4-((S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-{(1S,2R)-1-cyclohexylmethyl-2-hydroxy-3-[(1-oxy-1-aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methanesulfonyl]-propylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid tert-butyl ester (142843-22-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / ethanol / 3 h / 90 °C

2: ethanolic HCl / 1 h / Ambient temperature

3: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), triethylamine / CH₂Cl₂ / 17 h / Ambient temperature

4: 40 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane;

DOI:10.1021/jm00093a009

Reference yield:

(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane (107202-61-9) → 4-((S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-{(1S,2R)-1-cyclohexylmethyl-2-hydroxy-3-[(1-oxy-1-aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methanesulfonyl]-propylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid tert-butyl ester (142843-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / triethylamine / ethanol

2: 75 percent / ethanol / 3 h / 90 °C

3: ethanolic HCl / 1 h / Ambient temperature

4: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), triethylamine / CH₂Cl₂ / 17 h / Ambient temperature

5: 40 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane;

DOI:10.1021/jm00093a009

upstream raw materials:

4-[(S)-2-{(1S,2R)-3-[(1-Aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methylsulfanyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester

quinuclidin-3-amine

(2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane

ethyl 2-<<(2R,3S)-3-<(tert-butoxycarbonyl)amino>-4-cyclohexyl-2-hydroxy-1-butyl>thio>acetate

Downstream raw materials:

{(S)-1-[(S)-1-{(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-[(1-oxy-1-aza-bicyclo[2.2.2]oct-3-ylcarbamoyl)-methanesulfonyl]-propylcarbamoyl}-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester