{(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 185509-03-9
• Molecular Formula: C₂₄H₃₂N₂O₄
• Molecular Weight: 412.529
• Mol file: 185509-03-9.mol

Synonyms:{(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Chemical Property of {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

There total 5 articles about {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + (S,S)-pseudoephedrine D-phenylalaninamide (170899-07-7) → {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (185509-03-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 0 ℃;

DOI:10.1016/0040-4039(95)02053-5

Reference yield:

benzyl bromide (100-39-0) + {[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-carbamic acid tert-butyl ester (185508-77-4) → {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (185509-03-9) + {(S)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Guidance literature:

With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1021/ja9624073

Reference yield:

BOC-glycine (4530-20-5) → {(R)-1-[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (185509-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 13.0 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

3: LDA, LiCl / tetrahydrofuran / 1 h / 0 °C

With triethylamine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja9624073

upstream raw materials:

di-tert-butyl dicarbonate

(S,S)-pseudoephedrine D-phenylalaninamide

benzyl bromide

{[((1S,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-carbamoyl]-methyl}-carbamic acid tert-butyl ester

Downstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

Boc-D-Phe-OH

(R)-tert-butyl-3-oxo-1-phenylbutan-2-ylcarbamate