(3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Base Information

• Chemical Name: (3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid
• CAS No.: 267230-44-4
• Molecular Formula: C25H28 N2 O6
• Molecular Weight: 452.507
• DSSTox Substance ID: DTXSID60434403
• Nikkaji Number: J1.337.499F
• Wikidata: Q82248816
• Mol file: 267230-44-4.mol

Synonyms:267230-44-4;(3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid;CID 10026865;(3R,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-3-carboxylic acid;(3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid;SCHEMBL742949;DTXSID60434403;MDJLYIHNKUJSBA-TZIWHRDSSA-N;MFCD09608142;AS-50622;CS-0053300;P10738;(3R,4S)-1-Boc-4-N-Fmoc-4-aminopyrrolidine-3-carboxylic acid;(3R)-4alpha-(9H-Fluorene-9-ylmethoxycarbonylamino)pyrrolidine-1,3beta-dicarboxylic acid 1-tert-butyl ester;(3R,4S)-1-(tert-Butoxycarbonyl)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pyrrolidine-3-carboxylic acid;(3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylicacid;(3R,4S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid;(3R,4S)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1,3-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl)ester

Chemical Property of (3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.627
• Boiling Point: 650.2°Cat760mmHg
• PKA: 4.17±0.40(Predicted)
• Flash Point: 347°C
• PSA: 105.17000
• Density: 1.33g/cm³
• LogP: 4.17400
• Storage Temp.: 2-8°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 452.19473662
• Heavy Atom Count: 33
• Complexity: 728

Purity/Quality:

97% ^*data from raw suppliers

(3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(C(C1)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H]([C@@H](C1)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)C(=O)O

Technology Process of (3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

There total 10 articles about (3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-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: 84.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (267230-43-3) → (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid (267230-44-4)

Guidance literature:

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester; With palladium on activated charcoal; hydrogen; In methanol; at 20 ℃; for 15h; under 1810.07 Torr;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; With sodium hydrogencarbonate; In water; acetone; at 20 ℃; for 28h; Further stages.;

DOI:10.1021/ja000093k

Reference yield:

(3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride (346610-81-9,267230-41-1) → (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid (267230-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Pd/C; H₂ / ethanol / 22 h / 20 °C / 2585.81 Torr

1.2: 90 percent / NaHCO₃ / acetone; H₂O / 14 h / 20 °C

2.1: LiOH / methanol; H₂O / 15 h / 0 °C

3.1: Pd/C; H₂ / methanol / 15 h / 20 °C / 1810.07 Torr

3.2: 84 percent / NaHCO₃ / acetone; H₂O / 28 h / 20 °C

With lithium hydroxide; palladium on activated charcoal; hydrogen; In methanol; ethanol; water; 1.1: Hydrogenolysis / 1.2: Acylation / 2.1: Hydrolysis / 3.1: Hydrogenolysis / 3.2: Acylation;

DOI:10.1021/ja000093k

Reference yield:

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (267230-42-2) → (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid (267230-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiOH / methanol; H₂O / 15 h / 0 °C

2.1: Pd/C; H₂ / methanol / 15 h / 20 °C / 1810.07 Torr

2.2: 84 percent / NaHCO₃ / acetone; H₂O / 28 h / 20 °C

With lithium hydroxide; palladium on activated charcoal; hydrogen; In methanol; water; 1.1: Hydrolysis / 2.1: Hydrogenolysis / 2.2: Acylation;

DOI:10.1021/ja000093k

upstream raw materials:

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

(3R,4S)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Downstream raw materials:

(3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester

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