28562-53-0 Usage
Chemical Properties
White crystalline powder
Uses
4-Acetoxy-2-azetidinone was used in the synthesis of derivatized cyclopentenes in high regio- and diastereoselectivity. It was also used as a heterocyclic synthon for antibiotic and anti-inflammatory agents.
Synthesis Reference(s)
Journal of the American Chemical Society, 112, p. 7820, 1990 DOI: 10.1021/ja00177a067Tetrahedron Letters, 29, p. 1409, 1988 DOI: 10.1016/S0040-4039(00)80310-X
Purification Methods
Dissolve it in CHCl3, dry (MgSO4) concentrate at 40o/70mm, or better at room temperature to avoid decomposition. Wash and stir the residual oil with hexane by decantation and discard the wash. Dry the oil at high vacuum when it should solidify, m 34o. It can be distilled at high vacuum, 80-82o/10-3mm, but this results in extensive losses. The purity can be checked by TLC using Merck Silica Gel F254 and eluting with EtOAc. The azetidinone has RF 0.38 (typical impurities have RF 0.67). The spots can be detected by the TDM spray. This is prepared from (A) 2.5g 4,4'-tetramethyldiaminodiphenylmethane (TDM) in 10mL AcOH and diluted with 50mL of H2O, (B) 5g KI in 100mL of H2O and (C) 0.3g ninhydrin in 10mL of AcOH and 90mL of H2O. The spray is prepared by mixing (A) and (B) with 1.5mL of (C) and stored in a brown bottle. [Clau et al. Justus Liebigs Ann Chem 539 1974, Michel et al. Org Synth 65 135 1987, Beilstein 21/12 V 4.]
Check Digit Verification of cas no
The CAS Registry Mumber 28562-53-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,5,6 and 2 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 28562-53:
(7*2)+(6*8)+(5*5)+(4*6)+(3*2)+(2*5)+(1*3)=130
130 % 10 = 0
So 28562-53-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H7NO3/c1-3(7)9-5-2-4(8)6-5/h5H,2H2,1H3,(H,6,8)
28562-53-0Relevant articles and documents
A Superior Procedure for the Preparation of 2-Azetidinones From Volatile Olefins
Hauser, Frank M.,Ellenberger, Suzanne R.
, p. 324 (1987)
The use of a pressure bottle for cycloaddition of chlorosulfonyl isocyanate with volatile olefins not only provides the azetidinones in significantly improved yield, but also greatly simplifies the experimental procedure.
N-acyl-β-lactam derivative, macromolecular compound, and photoresist composition
-
Paragraph 0258-0261, (2014/10/28)
Provided are N-acyl-β-lactam derivatives represented by the following general formula, from which a photoresist composition capable of controlling an acid diffusion length to be short is obtained; a polymer obtained by polymerizing the N-acyl-β-lactam derivative represented by the following general formula as one of starting materials; and a photoresist composition containing the polymer, where the structural variables are as defined herein.
Convergent synthesis of (2R,3R,8R,9R)-N-Boc-ADDA
Meiries, Sebastien,Marquez, Rodolfo
, p. 5015 - 5021 (2008/12/20)
(Figure Presented) The convergent synthesis of N-Boc-(2R,3R,8R,9R,4E,6E)-3- amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadenoic acid (enantio-N-Boc-ADDA) is reported. Our flexible approach takes advantage of highly efficient non-aldol aldol and cross-metathesis methodologies.
