phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate

Base Information

• Chemical Name: phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate
• CAS No.: 922705-77-9
• Molecular Formula: C₂₄H₂₄N₄O₅
• Molecular Weight: 448.478
• Mol file: 922705-77-9.mol

Synonyms:phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate

Chemical Property of phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate

There total 3 articles about phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate 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: 69.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Nα-benzyloxycarbonyl-Nα-methyl-Nε-phthaloyl-L-lysine (131451-44-0) → phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate (922705-77-9)

Guidance literature:

N^α-benzyloxycarbonyl-N^α-methyl-N^ε-phthaloyl-L-lysine; With 4-methyl-morpholine; chloroformic acid ethyl ester; In tetrahydrofuran; at -15 ℃; for 0.25h;

diazomethane; In tetrahydrofuran; dichloromethane; at -15 - 20 ℃;

DOI:10.1002/hlca.200690235

Reference yield:

Cbz-Lys(phthaloyl)-OH (37579-45-6) → phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate (922705-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CSA / toluene / Heating

2.1: Et₃SiH; CF₃COOH / CH₂Cl₂

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

3.2: 69 percent / tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

With 4-methyl-morpholine; triethylsilane; chloroformic acid ethyl ester; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/hlca.200690235

Reference yield:

phenylmethyl (4S)-4-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]-5-oxo-1,3-oxazolidine-3-carboxylate (300560-53-6) → phenylmethyl [(1S)-1-(diazoacetyl)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)pentyl]methylcarbamate (922705-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Et₃SiH; CF₃COOH / CH₂Cl₂

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

2.2: 69 percent / tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

With 4-methyl-morpholine; triethylsilane; chloroformic acid ethyl ester; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.200690235

upstream raw materials:

diazomethane

N^α-benzyloxycarbonyl-N^α-methyl-N^ε-phthaloyl-L-lysine

Cbz-Lys(phthaloyl)-OH

phenylmethyl (4S)-4-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]-5-oxo-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

(3S)-7-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)heptanoic acid