L-Valine, N-[1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl]-

Base Information

• Chemical Name: L-Valine, N-[1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl]-
• CAS No.: 65671-71-8
• Molecular Formula: C15H26N2O5
• Molecular Weight: 314.37700
• DSSTox Substance ID: DTXSID30471921
• Nikkaji Number: J2.559.968C
• Wikidata: Q82300619
• Mol file: 65671-71-8.mol

Synonyms:65671-71-8;L-Valine, N-[1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl]-;1-Boc-L-prolyl-L-valine;t-butoxycarbonylprolylvaline;SCHEMBL4391131;DTXSID30471921

Chemical Property of L-Valine, N-[1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl]-

Chemical Property:

• PSA: 99.43000
• LogP: 2.38950
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 314.18417193
• Heavy Atom Count: 22
• Complexity: 442

Purity/Quality:

1-Boc-L-prolyl-L-valine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)C1CCCN1C(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)OC(C)(C)C

Technology Process of L-Valine, N-[1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl]-

There total 9 articles about L-Valine, N-[1-[(1,1-dimethylethoxy)carbonyl]-L-prolyl]- 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: 85.0%

tert-butyl (2S)-2-((2S)-1-methoxy-3-methyl-1-oxo-butan-2-ylcarbamoyl)pyrrolidine-1-carboxylate (74912-90-6) → (S)?1?[(S)?2?[(tert?butoxycarbonyl)amino]?3?methylbutanoyl]pyrrolidine?2?carboxylic acid (65671-71-8)

Guidance literature:

With potassium hydroxide; In methanol; at 0 - 20 ℃; for 4h;

DOI:10.1016/j.tet.2013.04.078

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (S)?1?[(S)?2?[(tert?butoxycarbonyl)amino]?3?methylbutanoyl]pyrrolidine?2?carboxylic acid (65671-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HOBT, DCCD, 2.) alkali, Et₃N / 1.) THF, 0 deg C, 1 h; r.t., 1 h, 2.) chloroform, 0 deg C, 1 h; r.t., 1 h

2: 1 N aq. NaOH / dioxane / 2 h / Ambient temperature

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane;

Reference yield:

N-(tert-butoxycarbonyl)-L-prolyl-L-valine benzyl ester (53363-79-4) → (S)?1?[(S)?2?[(tert?butoxycarbonyl)amino]?3?methylbutanoyl]pyrrolidine?2?carboxylic acid (65671-71-8)

Guidance literature:

DOI:10.1107/S0567740880008242

upstream raw materials:

N-(tert-butoxycarbonyl)-L-prolyl-L-valine benzyl ester

tert-butyl (2S)-2-((2S)-1-methoxy-3-methyl-1-oxo-butan-2-ylcarbamoyl)pyrrolidine-1-carboxylate

1-(tert-butoxycarbonyl)-L-proline

L-valine methylester hydrochloride

Downstream raw materials:

Boc-Pro-Val-Arg(NO₂)-Gly-OBzl

rhodamine(Arg-(Cbz)2-Pro-Val-NHBoc)₂

C₂₈H₄₄N₄O₆