(3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one

Base Information

• Chemical Name: (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one
• CAS No.: 74213-38-0
• Molecular Formula: C₁₉H₂₆N₂O₂S
• Molecular Weight: 346.494
• Mol file: 74213-38-0.mol

Synonyms:(3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one

Chemical Property of (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one

There total 6 articles about (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one 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: 84.0%

(3R,4R)-3-amino-1-methylallyl-4-t-butylthioazetidin-2-one (120420-31-7) + phenylacetyl chloride (103-80-0) → (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one (74213-38-0)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h;

Reference yield: 46.0%

2-methyl-3-bromo-1-propene (1458-98-6) + cis-(4R)-t-butylthio-(3R)-phenylacetamidoazetidin-2-one (74213-37-9) → (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one (74213-38-0)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; tert-butyl alcohol; for 3h; ice-NaCl cooled temp.;

Reference yield:

(1S,5R)-3-benzyl-6-(2-bromo-1-hydroxy-2-methylpropyl)-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-7-one (74213-36-8,74243-81-5,104486-77-3) → (3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylthioazetidin-2-one (74213-38-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / Et₃N

2: 46 percent / tBuOK / dimethylformamide

With potassium tert-butylate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/c39800000034

upstream raw materials:

2-methyl-3-bromo-1-propene

cis-(4R)-t-butylthio-(3R)-phenylacetamidoazetidin-2-one

(3R,4R)-3-amino-1-methylallyl-4-t-butylthioazetidin-2-one

phenylacetyl chloride

Downstream raw materials:

(3R,4R)-1-methylallyl-3-phenylacetamido-4-t-butylsulphinylazetidin-2-one

(1S,5R,6R)-2,2-dimethyl-6-phenylacetamidopenam 1-oxide