(R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate

Base Information

• Chemical Name: (R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate
• CAS No.: 219752-75-7
• Molecular Formula: C₁₀H₁₈INO₄
• Molecular Weight: 343.162
• Hs Code.: 2924199090
• European Community (EC) Number: 805-394-5
• Wikidata: Q76415902
• Mol file: 219752-75-7.mol

Synonyms:219752-75-7;(R)-METHYL 2-((TERT-BUTOXYCARBONYL)AMINO)-4-IODOBUTANOATE;(R)-Boc-gamma-iodo-abu-ome;Methyl (2R)-4-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;(R)-2-(Boc-amino)-4-iodobutyric acid methyl ester;(R)-Boc-|A-Iodo-Abu-OMe;SCHEMBL13640201;AMY21560;FD6075;MFCD16294351;methyl (2R)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;BS-27791;A4712;CS-0209073;methyl (R)-2-((tert-butoxycarbonyl)amino)-4-iodobutanoate;methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-4-iodobutanoate;(R)-METHYL2-((TERT-BUTOXYCARBONYL)AMINO)-4-IODOBUTANOATE;Methyl (2R)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-iodobutanoate;(R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate (Boc-D-Abu(I)-OMe)

Chemical Property of (R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate

Chemical Property:

• Boiling Point: 369.6±32.0 °C(Predicted)
• PKA: 10.89±0.46(Predicted)
• PSA: 68.12000
• Density: 1.500±0.06 g/cm3(Predicted)
• LogP: 2.08220
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 343.02806
• Heavy Atom Count: 16
• Complexity: 250

Purity/Quality:

≥98%, ^*data from raw suppliers

(R)-Methyl2-((tert-butoxycarbonyl)amino)-4-iodobutanoate 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)NC(CCI)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CCI)C(=O)OC

Technology Process of (R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate

There total 8 articles about (R)-Methyl 2-((tert-butoxycarbonyl)amino)-4-iodobutanoate 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: 93.0%

methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate (177472-33-2) → methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-iodobutyrate (219752-75-7)

Guidance literature:

With sodium iodide; In acetone; for 20h; Ambient temperature;

DOI:10.1021/jo981895p

Reference yield: 56.0%

methyl (2R)-2-[(tert-butoxy)carbonylamino]-4-hydroxybutanoate (258351-86-9) → methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-iodobutyrate (219752-75-7)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-iodobutyrate (219752-75-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / dmap / water; tetrahydrofuran / 6 h / 20 °C / Cooling with ice

2.1: dicyclohexyl-carbodiimide / ethyl acetate / 4 h / 20 °C / Cooling with ice

3.1: sodium tetrahydroborate / water; tetrahydrofuran / 0.17 h / Cooling with ice

3.2: 20 °C

4.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 2 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; iodine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; dmap; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

upstream raw materials:

methyl (2R)-<(tert-butyloxycarbonyl)amino>-4-bromobutyrate

di-tert-butyl dicarbonate

(2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester

(R)-Aspartate α-methyl ester

Refernces

• 1、 Zeng, Binqi,Wong, Kenny K.,Pompliano, David L.,Reddy, Sreelatha,Tanner, Martin E.. "A phosphinate inhibitor of the meso-diaminopimelic acid-adding enzyme (MurE) of peptidoglycan biosynthesis". . p. 10081 - 10086. Retrieved 2007/10/03.