(R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 167102-63-8
• Molecular Formula: C12H21NO4
• Molecular Weight: 243.303
• DSSTox Substance ID: DTXSID001156973
• Nikkaji Number: J2.249.111C
• Mol file: 167102-63-8.mol

Synonyms:167102-63-8;(R)-TERT-BUTYL 4-ACETYL-2,2-DIMETHYLOXAZOLIDINE-3-CARBOXYLATE;Tert-butyl (4R)-4-acetyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate;(R)-tert-Butyl4-acetyl-2,2-dimethyloxazolidine-3-carboxylate;SCHEMBL3616471;OBEQVSYPZVGBHL-SECBINFHSA-N;DTXSID001156973;CS-0069200;A920898;(4R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4beta-acetyloxazolidine;(R)-4-acetyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester;1,1-Dimethylethyl (4R)-4-acetyl-2,2-dimethyl-3-oxazolidinecarboxylate

Chemical Property of (R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 243.14705815
• Heavy Atom Count: 17
• Complexity: 330

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1COC(N1C(=O)OC(C)(C)C)(C)C
• Isomeric SMILES: CC(=O)[C@H]1COC(N1C(=O)OC(C)(C)C)(C)C

Technology Process of (R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate

There total 22 articles about (R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate 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: 94.0%

(4R)-4-[(R)-1-hydroxyethyl]-2,2-dimethyl-N-(tert-butoxycarbonyl)-1,3-oxazolidine (156173-83-0) → (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone (167102-63-8,433683-01-3)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1039/a800571k

Reference yield: 92.0%

(4R)-(1-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (488727-69-1) → (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone (167102-63-8,433683-01-3)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; dimethyl sulfoxide; at -78 - 20 ℃;

DOI:10.1021/ol027019m

Reference yield: 86.0%

methyllithium (917-54-4) + (R)-N,O-isopropylidenyl-2-(N-tert-butyloxycarbonylamino)-3-oxo-propanamide-N,O-dimethyl-hydroxyamine (167102-62-7,1822572-30-4) → (R)-N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-oxo-2-butanone (167102-63-8,433683-01-3)

Guidance literature:

In tetrahydrofuran; ethyl acetate; at -65 ℃; for 1h;

DOI:10.1021/ja0126226

upstream raw materials:

methyllithium

(R)-N,O-isopropylidenyl-2-(N-tert-butyloxycarbonylamino)-3-oxo-propanamide-N,O-dimethyl-hydroxyamine

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

(4R)-2,2-dimethyl-N-(tert-butoxycarbonyl)-4-(1-trimethylsilyloxyvinyl)-1,3-oxazolidine

Downstream raw materials:

(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

C₁₈H₂₅NO₆

C₁₈H₂₃NO₅

(R)-4-(1-hydroxy-1-methyl-2-phenylethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester