(2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Base Information

• Chemical Name: (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
• CAS No.: 274693-83-3
• Molecular Formula: C₂₄H₃₃NO₄
• Molecular Weight: 399.53
• Mol file: 274693-83-3.mol

Synonyms:(2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property of (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

There total 4 articles about (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide 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:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide (159213-03-3) + 1-((S)-2-Iodo-1-methyl-ethoxymethyl)-4-methoxy-benzene (274693-82-2) → (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (274693-83-3) + (2S,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Guidance literature:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 1.33333h;

1-((S)-2-Iodo-1-methyl-ethoxymethyl)-4-methoxy-benzene; In tetrahydrofuran; at 0 - 20 ℃; for 72h;

DOI:10.1016/S0040-4039(00)00208-2

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (274693-83-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: TsOH

2.1: LiAlH₄

3.1: triphenylphosphine; iodine

4.1: LDA; LiCl / tetrahydrofuran / 1.33 h / -78 - 20 °C

4.2: tetrahydrofuran / 72 h / 0 - 20 °C

With lithium aluminium tetrahydride; iodine; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1.1: Etherification / 2.1: Reduction / 3.1: Iodination / 4.1: Metallation / 4.2: Alkylation;

DOI:10.1016/S0040-4039(00)00208-2

Reference yield:

(S)-2-(4-methoxybenzyloxy)propionic acid ethyl ester (144401-98-9) → (2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide (274693-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiAlH₄

2.1: triphenylphosphine; iodine

3.1: LDA; LiCl / tetrahydrofuran / 1.33 h / -78 - 20 °C

3.2: tetrahydrofuran / 72 h / 0 - 20 °C

With lithium aluminium tetrahydride; iodine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; 1.1: Reduction / 2.1: Iodination / 3.1: Metallation / 3.2: Alkylation;

DOI:10.1016/S0040-4039(00)00208-2

upstream raw materials:

N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpropionamide

1-((S)-2-Iodo-1-methyl-ethoxymethyl)-4-methoxy-benzene

O-(4-methoxybenzyl)-trichloroacetimidate

(S)-2-(4-methoxybenzyloxy)propionic acid ethyl ester

Downstream raw materials:

(2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanoic acid

(2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentanal

(2R,4S)-4-(4-Methoxy-benzyloxy)-2-methyl-pentan-1-ol

1-((E)-(1S,3R)-5-Iodo-1,3-dimethyl-pent-4-enyloxymethyl)-4-methoxy-benzene