(2S,4R)-4-BOC-AMINO PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER-HCL

Base Information

• Chemical Name: (2S,4R)-4-BOC-AMINO PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER-HCL
• CAS No.: 473806-21-2
• Molecular Formula: C₁₁H₂₀N₂O₄
• Molecular Weight: 244.291
• Mol file: 473806-21-2.mol

Synonyms:BOCCHEM BC-L-E188;4-tertbutyloxycarbonylamino-L-trans-proline methyl ester;

Chemical Property of (2S,4R)-4-BOC-AMINO PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER-HCL

Chemical Property:

• Boiling Point: 347.0±42.0 °C(Predicted)
• PKA: 11.90±0.40(Predicted)
• PSA: 76.66000
• Density: 1.13±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 1.13430
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

(2S,4R)-Methyl 4-(tert-butoxycarbonylamino)-pyrrolidine-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4R)-4-BOC-AMINO PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER-HCL

There total 11 articles about (2S,4R)-4-BOC-AMINO PYRROLIDINE-2-CARBOXYLIC ACID METHYL ESTER-HCL 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: 98.0%

1-benzyl 2-methyl (2S,4R)-4-(tert-butoxycarbonylamino)pyrrolidine-1,2-dicarboxylate (189215-90-5) → 4-tertbutyloxycarbonylamino-L-trans-proline methyl ester (473806-21-2,1279200-56-4)

Guidance literature:

With methanol; palladium on activated charcoal;

DOI:10.1039/b308581c

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → 4-tertbutyloxycarbonylamino-L-trans-proline methyl ester (473806-21-2,1279200-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / PPh₃; DIAD / tetrahydrofuran

2: 90 percent / NaN₃ / dimethylformamide

3: 93 percent / H₂; Ni / ethyl acetate

4: 98 percent / methanol; Pd/C

With methanol; palladium on activated charcoal; sodium azide; di-isopropyl azodicarboxylate; hydrogen; nickel; triphenylphosphine; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/b308581c

Reference yield:

(2S,4R)-N-1-(benzyloxycarbonyl)-4-azidoproline methyl ester (189215-89-2) → 4-tertbutyloxycarbonylamino-L-trans-proline methyl ester (473806-21-2,1279200-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / H₂; Ni / ethyl acetate

2: 98 percent / methanol; Pd/C

With methanol; palladium on activated charcoal; hydrogen; nickel; In ethyl acetate;

DOI:10.1039/b308581c

upstream raw materials:

1-benzyl 2-methyl (2S,4R)-4-(tert-butoxycarbonylamino)pyrrolidine-1,2-dicarboxylate

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

(2S,4R)-N-1-(benzyloxycarbonyl)-4-azidoproline methyl ester

4R-4-hydroxyproline

Downstream raw materials:

(2S,4R)-1-[2-(4-Benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-acetyl]-4-tert-butoxycarbonylamino-pyrrolidine-2-carboxylic acid methyl ester

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine-2-carboxylic acid

Refernces

• 1、 Jordan, Stephan,Schwemler, Christoph,Kosch, Winfried,Kretschmer, Axel,Schwenner, Eckhardt,Stropp, Udo,Mielke, Burkhard. "Synthesis of new building blocks for peptide nucleic acids containing monomers with variations in the backbone". . p. 681 - 686. Retrieved 2007/10/03.