(2S,4R)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-((tert-butoxycarbonyl)aMino)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4R)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-((tert-butoxycarbonyl)aMino)pyrrolidine-2-carboxylic acid
• CAS No.: 273222-06-3
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507
• Hs Code.: 2933998090
• Mol file: 273222-06-3.mol

Synonyms:(2S,4R)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-((tert-butoxycarbonyl)aMino)pyrrolidine-2-carboxylic acid;(4R)-4-(Boc-amino)-1-Fmoc-L-proline;1,2 Pyrrolidinedicarboxylic acid, 4-1,1 dimethylethoxy carbonyl amino, 1-9H fluoren-9ylmethyl ester (2S,4R)

Chemical Property of (2S,4R)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-((tert-butoxycarbonyl)aMino)pyrrolidine-2-carboxylic acid

Chemical Property:

• Melting Point: 85-87 °C
• Boiling Point: 650.5±55.0 °C(Predicted)
• PKA: 3.78±0.40(Predicted)
• PSA: 105.17000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 4.31650
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(2S,4R)-4-Aminopyrrolidine-2-carboxylic acid, 4-Boc, N1-Fmoc protected 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4R)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-((tert-butoxycarbonyl)aMino)pyrrolidine-2-carboxylic acid

There total 5 articles about (2S,4R)-1-(((9H-Fluoren-9-yl)Methoxy)carbonyl)-4-((tert-butoxycarbonyl)aMino)pyrrolidine-2-carboxylic 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: 78.7%

(2S,4R)-H-Amp(Boc)-OH (1279034-78-4,1279030-48-6,1279038-29-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylic acid (273222-06-3,1253790-74-7)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/chem.201303290

Reference yield: 41.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-tertbutyloxycarbonylamino-L-trans-proline methyl ester (473806-21-2,1279200-56-4) → (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylic acid (273222-06-3,1253790-74-7)

Guidance literature:

4-tertbutyloxycarbonylamino-L-trans-proline methyl ester; With sodium hydroxide; In methanol;

(fluorenylmethoxy)carbonyl chloride; With sodium carbonate; In 1,4-dioxane; water; Further stages.;

DOI:10.1039/b308581c

Reference yield:

(2S,4R)-Nα-Cbz-4-N-Boc-aminoproline benzyl ester (853063-25-9) → (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylic acid (273222-06-3,1253790-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethanol / 12 h / 20 °C

2: 2.05 g / Et₃N / H₂O; tetrahydrofuran; acetonitrile / 2 h / 20 °C

With hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; water; acetonitrile;

DOI:10.1021/jm050009h

upstream raw materials:

(2S,4R)-H-Amp(Boc)-OH

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(fluorenylmethoxy)carbonyl chloride

4-tertbutyloxycarbonylamino-L-trans-proline methyl ester