Hexanedioic acid, 2-azido-3-(4-methoxyphenyl)-, 6-(1,1-dimethylethyl) 1-methyl ester, (2S,3R)-

Base Information

• Chemical Name: Hexanedioic acid, 2-azido-3-(4-methoxyphenyl)-, 6-(1,1-dimethylethyl) 1-methyl ester, (2S,3R)-
• CAS No.: 600708-98-3
• Molecular Formula: C18H25N3O5
• Molecular Weight: 363.414
• Mol file: 600708-98-3.mol

Synonyms:

Chemical Property of Hexanedioic acid, 2-azido-3-(4-methoxyphenyl)-, 6-(1,1-dimethylethyl) 1-methyl ester, (2S,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexanedioic acid, 2-azido-3-(4-methoxyphenyl)-, 6-(1,1-dimethylethyl) 1-methyl ester, (2S,3R)-

There total 7 articles about Hexanedioic acid, 2-azido-3-(4-methoxyphenyl)-, 6-(1,1-dimethylethyl) 1-methyl ester, (2S,3R)- 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:

succinic acid mono-tert-butyl ester (15026-17-2) → (2S,3R)-2-azido-3-(4-methoxyphenyl)hexanedioic acid 6-tert-butyl ester 1-methyl ester (600708-98-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 74 percent / BH₃*Me₂S / tetrahydrofuran / 24 h / 20 °C

2.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.25 h / -75 °C

3.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C

4.1: CuBr*Me₂S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C

4.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C

4.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

5.1: 850 mg / NaN₃ / dimethylformamide / 4 h / 20 °C

6.1: LiOH*H₂O; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / -5 - 0 °C

7.1: 1.30 g / diethyl ether / 0.33 h / 0 °C

With lithium hydroxide; sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dimethylsulfide borane complex; dihydrogen peroxide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 2.1: Swern oxidation / 4.2: Michael addition;

DOI:10.1021/jo0340152

Reference yield:

tert-butyl 4-hydroxybutyrate (59854-12-5) → (2S,3R)-2-azido-3-(4-methoxyphenyl)hexanedioic acid 6-tert-butyl ester 1-methyl ester (600708-98-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.25 h / -75 °C

2.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C

3.1: CuBr*Me₂S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C

3.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C

3.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

4.1: 850 mg / NaN₃ / dimethylformamide / 4 h / 20 °C

5.1: LiOH*H₂O; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / -5 - 0 °C

6.1: 1.30 g / diethyl ether / 0.33 h / 0 °C

With lithium hydroxide; sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; dihydrogen peroxide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Swern oxidation / 3.2: Michael addition;

DOI:10.1021/jo0340152

Reference yield:

tert-butyl 4-oxo-butanoate (51534-77-1) → (2S,3R)-2-azido-3-(4-methoxyphenyl)hexanedioic acid 6-tert-butyl ester 1-methyl ester (600708-98-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 5.7 g / LiCl; diisopropylethylamine / acetonitrile / 24 h / 20 °C

2.1: CuBr*Me₂S / tetrahydrofuran; various solvent(s) / 0.5 h / -45 - -10 °C

2.2: tetrahydrofuran; various solvent(s) / 0.33 h / -15 - -10 °C

2.3: NBS / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

3.1: 850 mg / NaN₃ / dimethylformamide / 4 h / 20 °C

4.1: LiOH*H₂O; hydrogen peroxide / tetrahydrofuran; H₂O / 0.5 h / -5 - 0 °C

5.1: 1.30 g / diethyl ether / 0.33 h / 0 °C

With lithium hydroxide; sodium azide; copper(I) bromide dimethylsulfide complex; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile; 2.2: Michael addition;

DOI:10.1021/jo0340152

upstream raw materials:

diazomethane

succinic acid mono-tert-butyl ester

tert-butyl 4-hydroxybutyrate

tert-butyl 4-oxo-butanoate

Downstream raw materials:

(2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 6-tert-butyl ester 1-methyl ester

(2S,3R)-2-methoxycarbonylamino-3-(4-methoxyphenyl)hexanedioic acid 1-methyl ester