(2S, 3S)-2-azido-3-butanoic acid

Base Information

• Chemical Name: (2S, 3S)-2-azido-3-butanoic acid
• CAS No.: 156721-26-5
• Molecular Formula: C₂₁H₂₂N₄O₄S
• Molecular Weight: 426.496
• Mol file: 156721-26-5.mol

Synonyms:(2S, 3S)-2-azido-3-butanoic acid

Chemical Property of (2S, 3S)-2-azido-3-butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S, 3S)-2-azido-3-butanoic acid

There total 7 articles about (2S, 3S)-2-azido-3-butanoic acid 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: 72.0%

(3(2S, 3S), 4R)-3-<2-azido-3-(N-(2-mesitylenesulfonyl)-3-indolyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone (156769-33-4) → (2S, 3S)-2-azido-3-butanoic acid (156721-26-5)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)86957-X

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) → (2S, 3S)-2-azido-3-butanoic acid (156721-26-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / 1.6M butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C - 0 deg C, 55 min, 2.) 0 deg C, 1 h, then RT, 2 h

2: triethylamine / tetrahydrofuran / -78 deg C - 0 deg C, 1 h

3: 1.6M nBuLi in hexane / tetrahydrofuran / -78 - 21 °C

4: 1.) CuBr-Me₂S, methyl sulfide, 2.) N-bromosuccinimide / 1.) THF, ether, 0 deg C, 2 h, then RT, 0.5 h, 2.) THF, -78 deg C, 2, h, then 0 deg C, 0.5 h

5: 78 percent / tetramethylguanidinium azide / acetonitrile / 120 h / Ambient temperature

6: 72 percent / LiOH*H₂O, 30percent H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

With lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; dihydrogen peroxide; triethylamine; tetramethylguanidinum azide; In tetrahydrofuran; hexane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)86957-X

Reference yield:

(2-mesitylenesulfonyl)indole-3-acrylic acid (156721-17-4) → (2S, 3S)-2-azido-3-butanoic acid (156721-26-5)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran / -78 deg C - 0 deg C, 1 h

2: 1.6M nBuLi in hexane / tetrahydrofuran / -78 - 21 °C

3: 1.) CuBr-Me₂S, methyl sulfide, 2.) N-bromosuccinimide / 1.) THF, ether, 0 deg C, 2 h, then RT, 0.5 h, 2.) THF, -78 deg C, 2, h, then 0 deg C, 0.5 h

4: 78 percent / tetramethylguanidinium azide / acetonitrile / 120 h / Ambient temperature

5: 72 percent / LiOH*H₂O, 30percent H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

With lithium hydroxide; N-Bromosuccinimide; n-butyllithium; dimethylsulfide; dihydrogen peroxide; triethylamine; tetramethylguanidinum azide; In tetrahydrofuran; water; acetonitrile;

DOI:10.1016/S0040-4020(01)86957-X

upstream raw materials:

(3(2S, 3S), 4R)-3-<2-azido-3-(N-(2-mesitylenesulfonyl)-3-indolyl)-1-oxobutyl>-4-phenyl-2-oxazolidinone

2-mesitylenesulphonyl chloride

(2-mesitylenesulfonyl)indole-3-acrylic acid

(3(2E), 4R)-3-<3-(N-(2-mesitylenesulfonyl)-3-indolyl)-1-oxopropenyl>-4-phenyl-2-oxazolidinone