(4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 510713-92-5
• Molecular Formula: C₁₈H₂₃F₂NO₅
• Molecular Weight: 371.381
• Mol file: 510713-92-5.mol

Synonyms:(4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Chemical Property of (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

There total 7 articles about (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-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: 82.0%

(R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (510713-90-3) → (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-92-5)

Guidance literature:

With triethylsilane; dibenzoyl peroxide; In 1,4-dioxane; at 110 ℃; for 1h;

DOI:10.1016/j.bmcl.2009.01.076

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-92-5)

Guidance literature:

Multi-step reaction with 6 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

5: tetrahydrofuran / 48 h / 30 - 40 °C

6: 200 mg / Et₃SiH; benzoyl peroxide / dioxane / Heating

With triethylsilane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; boron trifluoride diethyl etherate; sodium bromide; zinc; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethyl acetate; acetone; toluene; 4: Reformatsky reaction;

DOI:10.1055/s-2002-35616

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → (4S)-4-(2-ethoxycarbonyl-2,2-difluoroethyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-92-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

2: tetrahydrofuran / 48 h / 30 - 40 °C

3: 200 mg / Et₃SiH; benzoyl peroxide / dioxane / Heating

With triethylsilane; zinc; dibenzoyl peroxide; In tetrahydrofuran; 1,4-dioxane; 1: Reformatsky reaction;

DOI:10.1055/s-2002-35616

upstream raw materials:

(R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

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

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

benzyl chloroformate

Downstream raw materials:

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

(S)-4-Benzyloxycarbonylamino-2,2-difluoro-pentanedioic acid 1-ethyl ester

(S)-2-((S)-4-Benzyloxycarbonylamino-2,2-difluoro-5-hydroxy-pentanoylamino)-pentanedioic acid 1-tert-butyl ester 5-(2-trimethylsilanyl-ethyl) ester

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