[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester
• CAS No.: 141463-19-6
• Molecular Formula: C₂₂H₃₃N₃O₃S
• Molecular Weight: 419.588
• Mol file: 141463-19-6.mol

Synonyms:[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester

Chemical Property of [(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester

There total 1 articles about [(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl 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: 65.0%

imidazo[1,5-a]pyridine-3-thiol (76259-00-2) + (2R,3S)-3-(t-butoxycarbonylamino)-4-cyclohexyl-1,2-epoxybutane (107202-61-9) → [(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester (141463-19-6)

Guidance literature:

With 4-methyl-morpholine; In acetonitrile; at 85 ℃; for 2h;

DOI:10.1021/jm00089a023

Reference yield:

[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester (141463-19-6) → {(S)-1-[(S)-1-[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propylcarbamoyl]-2-(1H-imidazol-4-yl)-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) trifluoroacetic acid, 2.) triethylamine / 1.) RT, 30 min, 2.) CH₂Cl₂

2: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 3.5 h / Ambient temperature

3: 66 percent / NH₃ gas / methanol / 2 h / Ambient temperature

With ammonia; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;

DOI:10.1021/jm00089a023

Reference yield:

[(1S,2R)-1-Cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propyl]-carbamic acid tert-butyl ester (141463-19-6) → 4-{(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-2-[(1S,2R)-1-cyclohexylmethyl-2-hydroxy-3-(imidazo[1,5-a]pyridin-3-ylsulfanyl)-propylcarbamoyl]-ethyl}-imidazole-1-carboxylic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) trifluoroacetic acid, 2.) triethylamine / 1.) RT, 30 min, 2.) CH₂Cl₂

2: (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / CH₂Cl₂ / 3.5 h / Ambient temperature

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm00089a023

upstream raw materials:

imidazo[1,5-a]pyridine-3-thiol

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