(R)-tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate

Base Information

• Chemical Name: (R)-tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate
• CAS No.: 380886-36-2
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 291.304
• DSSTox Substance ID: DTXSID301133740
• Nikkaji Number: J1.660.781I
• Mol file: 380886-36-2.mol

Synonyms:380886-36-2;(R)-tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate;Tert-butyl (2R)-2-(1,3-dioxoisoindol-2-yl)oxypropanoate;Propanoic acid,2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,1,1-dimethylethyl ester,(2R)-;PROPANOIC ACID, 2-[(1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)OXY]-, 1,1-DIMETHYLETHYL ESTER, (2R)-;SCHEMBL17093931;APBDROVGLRLEDJ-SECBINFHSA-N;DTXSID301133740;(R)-2-(Phthalimidyloxy)propanoic acid tert-butyl ester;(R)-tert-Butyl2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate;1,1-Dimethylethyl (2R)-2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]propanoate

Chemical Property of (R)-tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate

Chemical Property:

• Vapor Pressure: 1.76E-06mmHg at 25°C
• Melting Point: 97-98 °C
• Boiling Point: 396.1°C at 760 mmHg
• Flash Point: 193.3°C
• PSA: 72.91000
• Density: 1.26g/cm³
• LogP: 1.88230
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 291.11067264
• Heavy Atom Count: 21
• Complexity: 430

Purity/Quality:

98% ^*data from raw suppliers

(2R)-2-[(1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)OXY]-PROPANOIC ACID-1,1-DIMETHYLETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)OC(C)(C)C)ON1C(=O)C2=CC=CC=C2C1=O
• Isomeric SMILES: C[C@H](C(=O)OC(C)(C)C)ON1C(=O)C2=CC=CC=C2C1=O

Technology Process of (R)-tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate

There total 3 articles about (R)-tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate 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: 69.0%

N-hydroxyphthalimide (524-38-9) + (+)-tert-butyl D-lactate (13650-70-9) → (R)-tert-butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate (380886-36-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo010376a

Reference yield:

N-hydroxyphthalimide (524-38-9) + (S)-tert-butyl 2-chloropropanoate (101617-24-7) → (R)-tert-butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate (380886-36-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 40 ℃; for 88h;

Reference yield:

(?)-(2S)-acetoxypropionic acid tert-butyl ester (120444-05-5,32376-44-6) → (R)-tert-butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate (380886-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / methanol; H₂O / 12 h / 20 °C

2: 69 percent / DEAD; PPh₃ / tetrahydrofuran

With potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo010376a

upstream raw materials:

N-hydroxyphthalimide

(+)-tert-butyl D-lactate

(?)-(2S)-acetoxypropionic acid tert-butyl ester

(S)-tert-butyl 2-chloropropanoate

Downstream raw materials:

D-tert-butyl 2-p-chlorophenylcarbonyl-aminoxy-propanoate

(R)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propionamide

(R)-2-phthalimidooxypropanoic acid