tert-Butyl (S)-4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxo-3-(((phenylmethoxy)carbonyl)amino)butyrate

Base Information

• Chemical Name: tert-Butyl (S)-4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxo-3-(((phenylmethoxy)carbonyl)amino)butyrate
• CAS No.: 3338-32-7
• Molecular Formula: C20H24N2O8
• Molecular Weight: 420.419
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID00955001
• Mol file: 3338-32-7.mol

Synonyms:tert-Butyl (S)-4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxo-3-(((phenylmethoxy)carbonyl)amino)butyrate;4-O-tert-butyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)butanedioate;SCHEMBL17177676;DTXSID00955001;EINECS 222-080-8;4-O-tert-butyl 1-O-(2,5-dioxopyrrolidin-1-yl) 2-(phenylmethoxycarbonylamino)butanedioate;FT-0650929;A875313;Z-L-aspartic acid beta-tert.butyl ester alpha- N-hydroxysuccinimide ester;(S)-4-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-(((benzyloxy)carbonyl)amino)succinate;4-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) N-[(benzyloxy)(hydroxy)methylidene]aspartate

Chemical Property of tert-Butyl (S)-4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxo-3-(((phenylmethoxy)carbonyl)amino)butyrate

Chemical Property:

• Melting Point: 150-152 °C
• Refractive Index: 1.559
• PKA: 10.03±0.46(Predicted)
• PSA: 128.31000
• Density: 1.322 g/cm³
• LogP: 1.94920
• Storage Temp.: −20°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 420.15326573
• Heavy Atom Count: 30
• Complexity: 663

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-4-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-(((benzyloxy)carbonyl)amino)succinate 95+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2=CC=CC=C2

Technology Process of tert-Butyl (S)-4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxo-3-(((phenylmethoxy)carbonyl)amino)butyrate

There total 2 articles about tert-Butyl (S)-4-((2,5-dioxo-1-pyrrolidinyl)oxy)-4-oxo-3-(((phenylmethoxy)carbonyl)amino)butyrate 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:

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Z-D(tBu)-OH (5545-52-8) → Z-Asp(OtBu)-OSu (3338-32-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1002/chem.201302732

Reference yield:

→ Z-Asp(OtBu)-OSu (3338-32-7)

Guidance literature:

Z-Asp(-OtBut), N-Hydroxy-succinimid, N,N'-Dicyclohexylcarbodiimid, Dioxan;

DOI:10.1021/ja01081a041

Reference yield: 100.0%

2,5,8,11,14,17,20-heptaoxadocosan-22-amine (170572-38-0,80506-64-5,869718-87-6) + Z-Asp(OtBu)-OSu (3338-32-7) → tert-butyl (25S)-25-{[(benzyloxy)carbonyl]amino}-24-oxo-2,5,8,11,14,17,20-heptaoxa-23-azaheptacosan-27-oate

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

Z-D(tBu)-OH

Downstream raw materials:

N-Benzyloxycarbonyl-(Asp-β-tert.-butylester)-(Asp-β-tert.-butylester)-(Asp-β-tert.-butylester)--Ile-Val-Gly-tert.-butylester

N-Benzyloxycarbonyl-(Asp-β-tert.-butylester)-(Asp-β-tert.-butylester)-(Asp-β-tert.-butylester)-(Asp-β-tert.-butylester)--Ile-Val-Gly-tert.-butylester

aspartylglycine

(S)-2-((S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionylamino)-6-tert-butoxycarbonylamino-hexanoic acid

Refernces

• 1、 HOFMANN,HAAS,SMITHERS,ZANETTI. "STUDIES ON POLYPEPTIDES. XXXI. SYNTHETIC PEPTIDES RELATED TO THE". . p. 631 - 639. Retrieved 2007/10/05.