3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[3,3,3-trifluoro-2-[(phenylmethoxy)methyl]propyl]-, 1,1-dimethylethyl ester, (4R)-

Base Information

• Chemical Name: 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[3,3,3-trifluoro-2-[(phenylmethoxy)methyl]propyl]-, 1,1-dimethylethyl ester, (4R)-
• CAS No.: 497103-69-2
• Molecular Formula: C21H30F3NO4
• Molecular Weight: 417.469
• Mol file: 497103-69-2.mol

Synonyms:

Chemical Property of 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[3,3,3-trifluoro-2-[(phenylmethoxy)methyl]propyl]-, 1,1-dimethylethyl ester, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[3,3,3-trifluoro-2-[(phenylmethoxy)methyl]propyl]-, 1,1-dimethylethyl ester, (4R)-

There total 3 articles about 3-Oxazolidinecarboxylic acid, 2,2-dimethyl-4-[3,3,3-trifluoro-2-[(phenylmethoxy)methyl]propyl]-, 1,1-dimethylethyl ester, (4R)- 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: 95.0%

benzyl bromide (100-39-0) + 2-trifluoromethyl-3-[(4R)-N-[(1,1-dimethyl)ethoxycarbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]propanol (497103-65-8) → 1-benzyloxy-2-trifluoromethyl-3-[(4R)-N-[(1,1-dimethyl)ethoxycarbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]propane (497103-69-2)

Guidance literature:

2-trifluoromethyl-3-[(4R)-N-[(1,1-dimethyl)ethoxycarbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]propanol; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.333333h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 5h; Further stages.;

DOI:10.1039/b206719f

Reference yield:

(R)-4-((Z)-2-Ethoxycarbonyl-3,3,3-trifluoro-propenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → 1-benzyloxy-2-trifluoromethyl-3-[(4R)-N-[(1,1-dimethyl)ethoxycarbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]propane (497103-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / Raney-Ni / aq. methanol / 20 °C

2.1: 2.30 g / LiAlH₄ / diethyl ether / 0 °C

3.1: Bu₄NI; NaH / tetrahydrofuran / 0.33 h / 0 - 20 °C

3.2: 95 percent / tetrahydrofuran / 5 h / 20 °C

With lithium aluminium tetrahydride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; nickel; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1039/b206719f

Reference yield:

ethyl 3-[(S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-2-(trifluoromethyl)propanoate (496848-29-4) → 1-benzyloxy-2-trifluoromethyl-3-[(4R)-N-[(1,1-dimethyl)ethoxycarbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]propane (497103-69-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2.30 g / LiAlH₄ / diethyl ether / 0 °C

2.1: Bu₄NI; NaH / tetrahydrofuran / 0.33 h / 0 - 20 °C

2.2: 95 percent / tetrahydrofuran / 5 h / 20 °C

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether;

DOI:10.1039/b206719f

upstream raw materials:

benzyl bromide

2-trifluoromethyl-3-[(4R)-N-[(1,1-dimethyl)ethoxycarbonyl]-2,2-dimethyl-1,3-oxazolidin-4-yl]propanol

ethyl 3-[(S)-3-(tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-yl]-2-(trifluoromethyl)propanoate

Downstream raw materials:

(2R)-2-[N-(1,1-dimethyl)ethoxycarbonylamino]-5-benzyloxy-4-trifluoromethylpentanol

(2R,4R)-1-(tert-butoxycarbonyl)-4-(trifluoromethyl) pyrrolidine-2-carboxylic acid

(2R,4S)-N-[(1,1-dimethyl)ethoxycarbonyl]-4-trifluoromethyl-D-proline

(2R,4R)-2-[N-(1,1-dimethyl)ethoxycarbonylamino]-1-tert-butyldimethylsilyloxy-5-benzyloxy-4-trifluoromethylpentane