(R)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID

Base Information

• Chemical Name: (R)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID
• CAS No.: 161891-81-2
• Molecular Formula: C14H17NO5
• Molecular Weight: 279.293
• Mol file: 161891-81-2.mol

Synonyms:(R)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID;(S)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID

Chemical Property of (R)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID

Chemical Property:

• Boiling Point: 447.1±45.0 °C(Predicted)
• PKA: 3.53±0.40(Predicted)
• PSA: 76.07000
• Density: 1.270±0.06 g/cm3(Predicted)
• LogP: 1.78260

Purity/Quality:

97% ^*data from raw suppliers

(S)-3-((Benzyloxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID

There total 4 articles about (R)-3-((BENZYLOXY)CARBONYL)-2,2-DIMETHYLOXAZOLIDINE-4-CARBOXYLIC ACID 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: 92.0%

N-(benzyloxycarbonyl)-L-serine (1145-80-8) + 2,2-dimethoxy-propane (77-76-9) → (S)-3-((benzyloxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid (161891-81-2)

Guidance literature:

With boron trifluoride diethyl etherate; In acetone; for 3h; Inert atmosphere;

DOI:10.1021/ol900893e

Reference yield:

N-(benzyloxycarbonyl)-L-serine (1145-80-8) → (S)-3-((benzyloxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid (161891-81-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / KHCO₃ / dimethylformamide / 7 h / 0 - 20 °C

2: 100 percent / TsOH / acetone / 12 h / 20 °C

3: 100 percent / LiOH / H₂O; dioxane / 4 h / 0 - 20 °C

With lithium hydroxide; potassium hydrogencarbonate; toluene-4-sulfonic acid; In 1,4-dioxane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1246/cl.2001.102

Reference yield:

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → (S)-3-((benzyloxy)carbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid (161891-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / TsOH / acetone / 12 h / 20 °C

2: 100 percent / LiOH / H₂O; dioxane / 4 h / 0 - 20 °C

With lithium hydroxide; toluene-4-sulfonic acid; In 1,4-dioxane; water; acetone;

DOI:10.1246/cl.2001.102

upstream raw materials:

N-(benzyloxycarbonyl)-L-serine

2,2-dimethoxy-propane

N-benzyloxycarbonyl-L-serine methyl ester

benzyl chloroformate

Downstream raw materials:

2-[(S)-1-{(S)-2-[((S)-3-Benzyloxycarbonyl-2,2-dimethyl-oxazolidine-4-carbonyl)-amino]-3-hydroxy-3-methyl-butyrylamino}-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-oxazole-4-carboxylic acid methyl ester

C₂₅H₂₉ClN₂O₅

(S)-4-((E)-(R)-3-ethoxycarbonyl-1-hydroxymethyl-2-methyl-allylcarbamoyl)-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

(S)-2-{[2-((S)-1-Benzyloxycarbonylamino-2-triethylsilanyloxy-ethyl)-5-methyl-oxazole-4-carbonyl]-amino}-3-(tert-butyl-diphenyl-silanyloxy)-propionic acid methyl ester