Carbamic acid, N-[(1S)-1-(2-diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)but yl]-N-methyl-, phenylmethyl ester

Base Information

• Chemical Name: Carbamic acid, N-[(1S)-1-(2-diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)but yl]-N-methyl-, phenylmethyl ester
• CAS No.: 922705-76-8
• Molecular Formula: C23H22N4O5
• Molecular Weight: 434.451
• Mol file: 922705-76-8.mol

Synonyms:

Chemical Property of Carbamic acid, N-[(1S)-1-(2-diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)but yl]-N-methyl-, phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, N-[(1S)-1-(2-diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)but yl]-N-methyl-, phenylmethyl ester

There total 3 articles about Carbamic acid, N-[(1S)-1-(2-diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)but yl]-N-methyl-, phenylmethyl 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: 53.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2S)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid (165105-56-6) → phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate (922705-76-8)

Guidance literature:

(2S)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid; 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-Orn(NPhth)-OH (7767-00-2) → phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate (922705-76-8)

Guidance literature:

Multi-step reaction with 3 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

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-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)propyl]-5-oxo-1,3-oxazolidine-3-carboxylate (167016-72-0) → phenylmethyl [(1S)-1-(diazoacetyl)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)butyl]methylcarbamate (922705-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 63 percent / Et₃SiH; CF₃COOH / CH₂Cl₂

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

2.2: 53 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

(2S)-5-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid

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

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

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