(R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER

Base Information

• Chemical Name: (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER
• CAS No.: 660852-86-8
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.276
• Mol file: 660852-86-8.mol

Synonyms:(R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER;(R)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID

Chemical Property of (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER

Chemical Property:

• Boiling Point: 358.2±42.0 °C(Predicted)
• PKA: 3.55±0.40(Predicted)
• PSA: 76.07000
• Density: 1.175±0.06 g/cm3(Predicted)
• LogP: 1.38090

Purity/Quality:

97% ^*data from raw suppliers

(R)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER

There total 7 articles about (R)-2,2-DIMETHYL-OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL 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: 99.0%

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate (108149-60-6,95715-86-9) → (4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (660852-86-8,301155-28-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 5.66667h;

DOI:10.1016/j.tetasy.2004.11.035

Reference yield: 88.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) + 2,2-dimethoxy-propane (77-76-9) → (4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (660852-86-8,301155-28-2)

Guidance literature:

With sulfuric acid; In acetone; at 0 - 30 ℃; for 0.5h;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-4-carboxylic acid (660852-86-8,301155-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaHCO₃ / tetrahydrofuran / 12 h / 20 °C

2: 4.56 g / BF₃*Et₂O / acetone / 2 h / 20 °C

3: aq. LiOH / methanol / 6 h / 0 - 20 °C

With lithium hydroxide; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; acetone;

DOI:10.1021/jm060405f

upstream raw materials:

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

di-tert-butyl dicarbonate

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

Downstream raw materials:

(R)-4-(2-benzoyl-phenylcarbamoyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

4-(methoxymethylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

C₁₉H₂₆N₂O₅

C₃₉H₄₆BrF₂NO₉