2,3-methanopyroglutamic acid

Base Information

• Chemical Name: 2,3-methanopyroglutamic acid
• CAS No.: 116447-40-6
• Molecular Formula: C₆H₇NO₃
• Molecular Weight: 141.126
• Mol file: 116447-40-6.mol

Synonyms:2-Azabicyclo[3.1.0]hexane-1-carboxylicacid, 3-oxo-, (?à)-

Chemical Property of 2,3-methanopyroglutamic acid

Chemical Property:

• Vapor Pressure: 6.33E-10mmHg at 25°C
• Boiling Point: 464.7°Cat760mmHg
• Flash Point: 234.9°C
• PSA: 69.89000
• Density: 1.621g/cm³
• LogP: -0.37450

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3-methanopyroglutamic acid

There total 14 articles about 2,3-methanopyroglutamic 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: 88.0%

methyl 2,3-methanopyroglutamate (116447-39-3,126484-94-4) → 2,3-methanopyroglutamic acid (116447-40-6,126484-92-2,145306-57-6,145306-58-7)

Guidance literature:

With sodium hydroxide; In methanol; for 1h;

DOI:10.1016/S0040-4020(01)89074-8

Reference yield: 55.0%

γ-methyl N-benzyloxycarbonyl-(Z)-2,3-methanoglutamic acid α-benzyl ester (145241-91-4) → (+/-)-2,3-methanopyroglutamic acid (116447-40-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; for 3h; under 760 Torr; Ambient temperature;

DOI:10.1246/bcsj.65.2668

Reference yield:

N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamate (104754-53-2) → (+/-)-2,3-methanopyroglutamic acid (116447-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CH₂Cl₂; diethyl ether / 1.) -20 deg C, 2 h, 2.) RT, 12 h

2: 88 percent / CH₂Cl₂ / 3 h / Irradiation

3: 55 percent / H₂ / 5percent Pd/C / methanol; acetic acid / 3 h / 760 Torr / Ambient temperature

With hydrogen; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetic acid;

DOI:10.1246/bcsj.65.2668

upstream raw materials:

methyl 2,3-methanopyroglutamate

dimethyl 2-ketoglutarate

methyl γ-methyl-α-(N-benzyloxycarbonyl)-α-dehydroglutamate

dimethyl N-benzyloxycarbonyl-2,3-methanoglutamate

Downstream raw materials:

(-)-(Z)-2,3-methano-L-glutamic acid

(+)-(2R,3R)-2,3-methanoglutamic acid

2,3-methanopyroglutamic acid N-methyl amide