(3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid

Base Information

• Chemical Name: (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid
• CAS No.: 922705-78-0
• Molecular Formula: C₂₃H₂₄N₂O₆
• Molecular Weight: 424.453
• Mol file: 922705-78-0.mol

Synonyms:(3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid

Chemical Property of (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid

There total 2 articles about (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid 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: 72.0%

phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate (922705-76-8) → (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid (922705-78-0)

Guidance literature:

With silver trifluoroacetate; In 1,4-dioxane; water; for 0.5h; sonication;

DOI:10.1002/hlca.200690235

Reference yield:

Cbz-Orn(NPhth)-OH (7767-00-2) → (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid (922705-78-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / CSA / toluene / Heating

2.1: 63 percent / Et₃SiH; CF₃COOH / CH₂Cl₂

3.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

3.2: 53 percent / tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

4.1: 72 percent / CF₃COOAg / dioxane; H₂O / 0.5 h / sonication

With 4-methyl-morpholine; triethylsilane; silver trifluoroacetate; chloroformic acid ethyl ester; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 4.1: Wolff rearrangement;

DOI:10.1002/hlca.200690235

Reference yield: 43.0%

(3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid (922705-78-0) + tert-butyl alcohol (75-65-0) → 1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate (922706-06-7)

Guidance literature:

With dmap; di-tert-butyl dicarbonate; at 20 ℃; for 20h;

DOI:10.1002/hlca.200690235

upstream raw materials:

phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate

Cbz-Orn(NPhth)-OH

Downstream raw materials:

1,1-dimethylethyl (3S)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoate