(2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate
• CAS No.: 253307-68-5
• Molecular Formula: C13H24N2O5
• Molecular Weight: 288.344
• DSSTox Substance ID: DTXSID601126809
• Nikkaji Number: J1.964.079E
• Mol file: 253307-68-5.mol

Synonyms:253307-68-5;DTXSID601126809;(2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate;(4R)-1-[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]-4-hydroxy-L-proline methyl ester

Chemical Property of (2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate

Chemical Property:

• PSA: 88.10000
• LogP: 0.44810
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 288.16852187
• Heavy Atom Count: 20
• Complexity: 353

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCN1CC(CC1C(=O)OC)O
• Isomeric SMILES: CC(C)(C)OC(=O)NCCN1C[C@@H](C[C@H]1C(=O)OC)O

Technology Process of (2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate

There total 1 articles about (2S,4R)-Methyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-4-hydroxypyrrolidine-2-carboxylate 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: 60.0%

2-(tert-butoxycarbonylamino)ethyl bromide (39684-80-5) + L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → 1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester (253307-68-5)

Guidance literature:

In acetonitrile;

DOI:10.1021/ol990835i

Reference yield: 80.0%

benzoic acid (65-85-0,8013-63-6) + 1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester (253307-68-5) → 1-N-(2-(Boc-amino)ethyl)-4S-O-benzoyl-2S-proline methyl ester

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 5h;

DOI:10.1016/j.tetlet.2003.12.072

Reference yield: 70.0%

1-(N-[2-(tert-butoxycarbonylamino)ethyl])-4-(R)-hydroxy-2-(S)-proline methyl ester (253307-68-5) + 4-nitro-benzoic acid (62-23-7) → (2S,4S)-1-(2-tert-Butoxycarbonylamino-ethyl)-4-(4-nitro-benzoyloxy)-pyrrolidine-2-carboxylic acid methyl ester

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 10h;

DOI:10.1016/j.tetlet.2003.12.072

upstream raw materials:

2-(tert-butoxycarbonylamino)ethyl bromide

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

C₂₅H₃₂N₄O₇

4-(4-benzyloxycarbonylamino-2-oxo-2H-pyrimidin-1-yl)-1-(2-tert-butoxycarbonylamino-ethyl)-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

1-(N-[tert-butoxycarbonylaminoethyl])-(4S)-(N⁴-benzyloxycarbonylcytosin-1-yl)-2-(S)-proline methyl ester