(2R,4R)-4-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,4R)-4-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS No.: 1018332-24-5
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.507
• Mol file: 1018332-24-5.mol

Synonyms:N-Boc-cis-4-N-Fmoc-amino-D-proline;(4R)-1-Boc-4-(Fmoc-amino)-D-proline

Chemical Property of (2R,4R)-4-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• PSA: 108.66000
• LogP: 4.13000

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R,?4R)?-?1-?Boc-?N-?Fmoc-?4-?amino-?pyrrolidine-?2-?carboxylic Acid can be used as reactant/reagent in synthetic preparation of KMI-008 peptide derivatives and proline-based peptidomimetic analogs and determination of their activity as BACE1 inhibitors (β-secretase inhibitors). It can also be used as reagent/reactant for preparation of aminoproline residues for solid phase synthesis of integrin binding cyclic peptides by bromination, azidation and protection/deprotection protocol.

Technology Process of (2R,4R)-4-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

There total 4 articles about (2R,4R)-4-(((9H-fluoren-9-yl)Methoxy)carbonylaMino)-1-(tert-butoxycarbonyl)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:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (2R,4R)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (132622-98-1) → (2R,4R)-1-(tert-butoxycarbonyl)-4-N-(9-fluorenylmethoxycarbonyl)aminoproline (1018332-24-5)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm701214z

Reference yield:

(2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (147266-92-0,946610-68-0) → (2R,4R)-1-(tert-butoxycarbonyl)-4-N-(9-fluorenylmethoxycarbonyl)aminoproline (1018332-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate / methanol; water; N,N-dimethyl-formamide / 20 h / 0 - 20 °C / Inert atmosphere

2: diethylazodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran; toluene / 24 h / 0 - 20 °C / Inert atmosphere

3: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

4: sodium hydrogencarbonate / water; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene;

Reference yield:

(2R,4S)-2-benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate (481704-22-7) → (2R,4R)-1-(tert-butoxycarbonyl)-4-N-(9-fluorenylmethoxycarbonyl)aminoproline (1018332-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diethylazodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran; toluene / 24 h / 0 - 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

3: sodium hydrogencarbonate / water; tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With diphenyl phosphoryl azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; toluene;

upstream raw materials:

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

(2R,4R)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

(2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

(2R,4S)-2-benzyl 1-tert-butyl 4-hydroxypyrrolidine-1,2-dicarboxylate

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