(1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine

Base Information

• Chemical Name: (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine
• CAS No.: 1315594-67-2
• Molecular Formula: C₁₇H₂₃NO₄*C₂₀H₂₄N₂O₂
• Molecular Weight: 629.797
• Mol file: 1315594-67-2.mol

Synonyms:

Chemical Property of (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine

There total 4 articles about (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine 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: 36.0%

(1SR,2RS,3RS)-methyl 1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropanecarboxylate + quinindine (56-54-2,130-95-0,572-59-8,572-60-1,42151-59-7,47342-58-5,72402-50-7,72402-51-8,72402-52-9,72402-53-0,101143-86-6,101143-87-7,101143-88-8,146925-10-2) → (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine (1315594-67-2)

Guidance literature:

(1SR,2RS,3RS)-methyl 1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropanecarboxylate; With sodium hydroxide; In tetrahydrofuran; methanol; at 90 ℃; for 12h;

quinindine; In acetone;

DOI:10.1021/jm101609j

Reference yield:

(2RS,3RS)-dimethyl 2,3-dimethyl-2-phenylcyclopropane-1,1-dicarboxylate → (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine (1315594-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / tetrahydrofuran; methanol / 12 h / 20 °C

2: diphenyl phosphoryl azide; triethylamine / 12 h / 100 °C

3: sodium hydroxide / tetrahydrofuran; methanol / 12 h / 90 °C

With diphenyl phosphoryl azide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; 2: Curtius rearrangement;

DOI:10.1021/jm101609j

Reference yield:

C14H16O4 → (1S,2R,3R)-1-tert-butoxycarbonylamino-2,3-dimethyl-2-phenylcyclopropane-1-carboxylic acid quinidine (1315594-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl phosphoryl azide; triethylamine / 12 h / 100 °C

2: sodium hydroxide / tetrahydrofuran; methanol / 12 h / 90 °C

With diphenyl phosphoryl azide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; 1: Curtius rearrangement;

DOI:10.1021/jm101609j

upstream raw materials:

quinindine

(Z)-2-phenylbut-2-ene

Downstream raw materials:

C₁₉H₂₆N₂O₆S

C₁₆H₂₃NO₂

C₂₆H₃₁FN₄O₄S

(1S,2R,3R)-2,3-dimethyl-1-(8-fluoro-1,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole-2-sulfonylamino)-2-phenylcyclopropane-1-carboxylic acid