(2S, 4S)-BOC-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID

Base Information

• Chemical Name: (2S, 4S)-BOC-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID
• CAS No.: 221352-74-5
• Molecular Formula: C25H28 N2 O6
• Molecular Weight: 452.507
• Hs Code.: 29339900
• Mol file: 221352-74-5.mol

Synonyms:RARECHEM EM WB 0070;BOC-(2S,4S)-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID;(2S, 4S)-BOC-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID;(2S,4S)-FMOC-GAMMA-(BOC-AMINO)-PROLINE

Chemical Property of (2S, 4S)-BOC-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID

Chemical Property:

• Melting Point: 87-89℃
• PSA: 105.17000
• LogP: 4.31650
• Storage Temp.: Store at -15°C

Purity/Quality:

97% ^*data from raw suppliers

Boc-(2S,4S)-4-amino-1-Fmoc-pyrrolidine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-(2S,4S)-4-amino-1-Fmoc-pyrrolidine-2-carboxylic Acid is used to prepare low molecular weight cyclic peptides as inhibitors of SDF-1 binding to CXCR4. it is also used to design α-conotoxin analogs targeting α7 nicotinic acetylcholine receptors.

Technology Process of (2S, 4S)-BOC-4-AMINO-1-FMOC-PYRROLIDINE-2-CARBOXYLIC ACID

There total 12 articles about (2S, 4S)-BOC-4-AMINO-1-FMOC-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: 50.0%

di-tert-butyl dicarbonate (24424-99-5) + C20H20N2O4 → (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid (221352-74-5,1253790-74-7)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 0 - 20 ℃;

DOI:10.1111/cbdd.13743

Reference yield: 43.0%

(2S,4S)-methyl 4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylate (168263-82-9,1279200-56-4) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid (221352-74-5,1253790-74-7)

Guidance literature:

(2S,4S)-methyl 4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylate; 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,4S)-Nα-Cbz-4-N-Boc-aminoproline benzyl ester (853063-23-7) → (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid (221352-74-5,1253790-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethanol / 12 h / 20 °C

2: 1.18 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:

(fluorenylmethoxy)carbonyl chloride

(2S,4S)-4-tert-Butoxycarbonylamino-pyrrolidine-2-carboxylic acid

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

(2S,4S)-methyl 4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylate

Downstream raw materials:

C₃₂H₃₄N₂O₆

C₃₉H₄₆N₂O₆

C₃₂H₄₀N₂O₆

C₃₄H₃₈N₂O₄

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