methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate

Base Information

• Chemical Name: methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate
• CAS No.: 436843-91-3
• Molecular Formula: C₂₀H₁₉BrN₂O₆S
• Molecular Weight: 495.351
• Mol file: 436843-91-3.mol

Synonyms:methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate

Chemical Property of methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate

There total 1 articles about methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate 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: 63.0%

5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole (101085-25-0) + methyl N-benzenesulfonyl-L-serinate (221526-66-5) → methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate (436843-91-3)

Guidance literature:

With potassium carbonate; In acetonitrile; for 2h; Heating;

DOI:10.1021/jo010665z

Reference yield:

methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate (436843-91-3) → (6S)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-phenyl-5-(phenylsulfonyl)-5,6-dihydro[1,3]oxazolo[4,5-c]pyridin-7(4H)-one (436843-89-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84.4 percent / DMAP / CH₂Cl₂ / 25 °C

2: 60 percent / n-BuLi / hexane; tetrahydrofuran / -100 °C

With dmap; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo010665z

Reference yield:

methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]-3-hydroxypropanoate (436843-91-3) → (6S,7R)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-phenyl-5-(phenylsulfonyl)4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridin-7-ol (436843-90-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 84.4 percent / DMAP / CH₂Cl₂ / 25 °C

2: 60 percent / n-BuLi / hexane; tetrahydrofuran / -100 °C

3: 72 percent / NaBH₄ / tetrahydrofuran; ethanol / 2 h / 20 °C

With dmap; sodium tetrahydroborate; n-butyllithium; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jo010665z

upstream raw materials:

5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole

methyl N-benzenesulfonyl-L-serinate

Downstream raw materials:

(6S)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-phenyl-5-(phenylsulfonyl)-5,6-dihydro[1,3]oxazolo[4,5-c]pyridin-7(4H)-one

(6S,7R)-6-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-phenyl-5-(phenylsulfonyl)4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridin-7-ol