(4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 510713-88-9
• Molecular Formula: C₁₈H₂₃F₂NO₆
• Molecular Weight: 387.381
• Mol file: 510713-88-9.mol

Synonyms:(4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

There total 5 articles about (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 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: 79.0%

Ethyl bromodifluoroacetate (667-27-6) + (4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-88-9)

Guidance literature:

With zinc; In tetrahydrofuran; for 0.25h; Heating;

DOI:10.1055/s-2002-35616

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-88-9)

Guidance literature:

Multi-step reaction with 4 steps

1: BF₃*Et₂O / acetone

2: NaBH₄ / tetrahydrofuran; methanol

3: 87 percent / aq. NaClO; TEMPO; NaBr / ethyl acetate; toluene / 0.25 h / 0 °C

4: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; boron trifluoride diethyl etherate; sodium bromide; zinc; In tetrahydrofuran; methanol; ethyl acetate; acetone; toluene; 4: Reformatsky reaction;

DOI:10.1055/s-2002-35616

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-88-9)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. NaHCO₃ / ethyl acetate

2: BF₃*Et₂O / acetone

3: NaBH₄ / tetrahydrofuran; methanol

4: 87 percent / aq. NaClO; TEMPO; NaBr / ethyl acetate; toluene / 0.25 h / 0 °C

5: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; boron trifluoride diethyl etherate; sodium hydrogencarbonate; sodium bromide; zinc; In tetrahydrofuran; methanol; ethyl acetate; acetone; toluene; 5: Reformatsky reaction;

DOI:10.1055/s-2002-35616

upstream raw materials:

Ethyl bromodifluoroacetate

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

benzyl chloroformate

Downstream raw materials:

2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester

N-Boc-Abz-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester

N-Cbz-(2S)-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester

N-Cbz-difluorooxazolidine-γ-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester