(4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one

Base Information

• Chemical Name: (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one
• CAS No.: 135777-60-5
• Molecular Formula: C₁₅H₁₇F₂NO₃
• Molecular Weight: 297.302
• Mol file: 135777-60-5.mol

Synonyms:(4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one

Chemical Property of (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one

There total 6 articles about (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-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: 93.0%

ethyl (3R,4R)-3-benzylamino-2,2-difluoro-4,5-O-isopropylidenepentanoate (147633-27-0) → (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one (135777-60-5)

Guidance literature:

With tert-butylmagnesium chloride; In diethyl ether; 0 deg C, 30 min then r.t., overnight;

DOI:10.1016/S0040-4020(01)82003-2

Reference yield: 8.0%

Ethyl bromodifluoroacetate (667-27-6) + (S)-N-benzyl-2,3-O-isopropylidene-glyceraldimine (135821-68-0) → (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one (135777-60-5) + (S)-1-Benzyl-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-azetidin-2-one (147633-26-9) + ethyl (3R,4R)-3-benzylamino-2,2-difluoro-4,5-O-isopropylidenepentanoate (147633-27-0)

Guidance literature:

With zinc; In tetrahydrofuran; for 1h; Heating;

DOI:10.1016/S0040-4020(01)82003-2

Reference yield:

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (22323-80-4) → (4R)-1-benzyl-3,3-difluoro-4-<(4'R)-2',2'-dimethyl-1',3'-dioxolan>-azetidin-2-one (135777-60-5)

Guidance literature:

Multi-step reaction with 2 steps

2: 29 percent / activated Zn / tetrahydrofuran / 1 h / Heating

With zinc; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)82003-2

upstream raw materials:

Ethyl bromodifluoroacetate

(S)-N-benzyl-2,3-O-isopropylidene-glyceraldimine

ethyl (3R,4R)-3-benzylamino-2,2-difluoro-4,5-O-isopropylidenepentanoate

benzylamine

Downstream raw materials:

(4R)-1-benzyl-4-(t-butyloxycarbonyl)-3,3-difluoroazetidin-2-one

(3R)-3-benzylamino-2,2-difluorobutane-1,4-diol

t-butyl (2R)-2-benzylamino-3,3-difluoro-4-hydroxybutanoate

(4R)-1-benzyl-3,3-difluoro-4-<(1'R)-1',2'-dihydroxyethyl>azetidin-2-one