N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal

Base Information

• Chemical Name: N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal
• CAS No.: 110562-21-5
• Molecular Formula: C₁₅H₂₂N₂O₄
• Molecular Weight: 294.351
• Mol file: 110562-21-5.mol

Synonyms:N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal

Chemical Property of N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal

There total 15 articles about N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal 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: 98.5%

N-(3-methoxy-2-nitrobenzoyl)-L-prolinal dimethyl acetal (117082-63-0) → N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal (110562-21-5)

Guidance literature:

With hydrogen; palladium; In ethanol; for 18h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80968-6

Reference yield: 84.0%

2-amino-3-methoxybenzoic acid (3177-80-8) + L-prolinal dimethyl acetal hydrochloride (110575-88-7) → N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal (110562-21-5)

Guidance literature:

With diethyl cyanophosphonate; 4 A molecular sieve; triethylamine; In tetrahydrofuran; 0 gradC for 1 h. then room temp. for 40 min.;

DOI:10.1016/S0040-4039(00)85411-8

Reference yield:

3-methoxy-2-nitrobenzoic acid (4920-80-3) → N-(-3-methoxy-2-aminobenzoyl)-L-prolinal dimethyl acetal (110562-21-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / diethyl phosphorocyanidate, triethylamine / dimethylformamide / 1) 0 deg C, 0.5 h, 2) r.t., 2 days

2: 89 percent / LiCl, sodium borohydride, EtOH / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 19.5 h

3: 77 percent / sulfur trioxide-pyridine complex, DMSO, triethylamine / CH₂Cl₂ / 0.17 h / 10 - 20 °C

4: 79 percent / 0.4 M cerium chloride / methanol

5: 98.5 percent / H₂ / palladium black / ethanol / 18 h / Ambient temperature

With sodium tetrahydroborate; cerium(III) chloride; ethanol; diethyl cyanophosphonate; hydrogen; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; lithium chloride; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80968-6

upstream raw materials:

2-amino-3-methoxybenzoic acid

L-prolinal dimethyl acetal hydrochloride

N-(3-methoxy-2-nitrobenzoyl)-L-prolinal dimethyl acetal

2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)-6-methoxyaniline

Refernces

• 1、 Mori, Shigehiro,Aoyama, Toyohiko,Shioiri, Takayuki. "NEW METHOD AND REAGENTS IN ORGANIC SYNTHESIS. 65. A STEREOSELECTIVE SYNTHESIS OF TILIVALLINE". . p. 6111 - 6114. Retrieved 2007/10/02.