(S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 439589-26-1
• Molecular Formula: C₄₁H₅₈N₂O₇S
• Molecular Weight: 722.987
• Mol file: 439589-26-1.mol

Synonyms:(S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property of (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 9 articles about (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl 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: 85.0%

(+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-hydroxybicyclo[2.2.1]heptane-1-methanesulfonamide (99295-72-4) + (S)-2-(((benzyloxy)carbonyl)(4-methoxybenzyl)amino)propanoic acid (439589-23-8) → (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-26-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo025571j

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-14-7) → (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-26-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂ / Pd/C / methanol / 1 h / 20 °C / 1551.49 Torr

2.1: methanol / 2 h / 20 °C

2.2: NaBH₃CN; ZnCl₂ / methanol / 2 h / 20 °C

3.1: 94 percent / propylene oxide / tetrahydrofuran / 20 °C

4.1: 55 percent / BTPP / CH₂Cl₂ / 24 h / 20 °C

5.1: 2 N NaOH / methanol / 20 °C

5.2: HCl / H₂O / pH 3

6.1: 85 percent / dimethylaminopyridine; DCC / CH₂Cl₂ / 24 h / 20 °C

With dmap; sodium hydroxide; hydrogen; dicyclohexyl-carbodiimide; tert-butylimino-tri(pyrrolidino)phosphorane; methyloxirane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo025571j

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1: propylene oxide / CH₂Cl₂

2: 4 M HCl / ethyl acetate

3: 85 percent / dimethylaminopyridine; DCC / CH₂Cl₂ / 24 h / 20 °C

With hydrogenchloride; dmap; dicyclohexyl-carbodiimide; methyloxirane; In dichloromethane; ethyl acetate;

DOI:10.1021/jo025571j

upstream raw materials:

(+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-hydroxybicyclo[2.2.1]heptane-1-methanesulfonamide

(S)-2-(((benzyloxy)carbonyl)(4-methoxybenzyl)amino)propanoic acid

benzyl chloroformate

(S)-2-(4-Methoxy-benzylamino)-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Downstream raw materials:

(S)-2-(4-Methoxy-benzylamino)-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(S)-1-(4-Methoxy-benzyl)-2-methyl-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester