Uridine Diphosphate → 4-Oxoretinoic acid

HRID 915197

Reaction equation

HRID 915197 reaction equation
[Si](C)(C)(C)C.[CH3:6][C:7]1[CH:12]([OH:13])[CH2:11][CH2:10][C:9]([CH3:15])([CH3:14])[C:8]=1/[CH:16]=[CH:17]/[C:18](/[CH3:28])=[CH:19]/[CH:20]=[CH:21]/[C:22](/[CH3:27])=[CH:23]/[C:24]([OH:26])=[O:25].C1C(=O)NC(=O)N([C@@H]2O[C@H](COP(OP(O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=1>>[CH3:6][C:7]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]([CH3:14])([CH3:15])[C:8]=1/[CH:16]=[CH:17]/[C:18](/[CH3:28])=[CH:19]/[CH:20]=[CH:21]/[C:22](/[CH3:27])=[CH:23]/[C:24]([OH:26])=[O:25]

Participants

4

Reactant 3

HCID 6031Uridine DiphosphateHCID 6396TetramethylsilaneHCID 64386294-Hydroxyretinoic acid

Product 1

HCID 64370634-Oxoretinoic acid

Procedure

Melting points (mp) are determined with a Fischer-Johns melting point apparatus and are uncorrected. Proton magnetic resonance spectra (1H NMR) are recorded in CDCl3 on a Mac NMR 5.3 300 MHz spectrometer (internal standard Me4Si, (δ=0), and high resolution mass spectra (HRMS) are determined on a Kratos Aspect Systems instrument, EI mode. Elemental analyses are performed by Chemisar Laboratories Inc., Guelph, Ontario, Canada. TLC is done on silica gel GHLF precoated plates (250 microns) purchased from Analtech, while flash column chromatography (FCC) is performed on silica gel (Merck grade 9385, 230-400 mesh, 60 Å) according to Still's method. (Still, W. C.; Kahn, M.; Mitra, A. Rapid Chromatographic Technique for Preparative Separation with Moderate Resolution. J. Org. Chem., 43, 2923-2925, 1978). “Pet. ether” refers to light petroleum, bp 40-60° C. [11,12-3H] All-trans-retinoic acid (ATRA, 51.8 (Ci/mmol) is purchased from New England Nuclear Life Science Products, Inc., while unlabeled ATRA is purchased from Sigma-Aldrich Chemical Co., St. Louis, Mo. Liarozole fumarate is obtained from Janssen Pharmaceutica, Beerse, Belgium. (±)-4-Hydroxy-ATRA and 4-oxo-ATRA are prepared using a well-known technique (Samokyszyn, V. M.; Gall, W. E.; Zawada, G.; Freyaldenhoven, M. A.; Chen, G.; Mackenzie, P. I.; Tephly, T. R.; Radominska-Pandya, A. 4-Hydroxyretinoic Acid, a Novel Substrate for Human Liver Mcrosomal UDP-glucuronosyltransferase(s) and Recombinant UGT2B7. J. Biol. Chem. 2000, 275, 6908-6914.)

Workup

  1. customRapid Chromatographic Technique for Preparative Separation with Moderate Resolution

Sources & evidence

ORD record
ord-0091c555f5884879aaceb097a390676d
Source dataset
uspto-grants-2007_09
Patent number
US07265143B2

Linked notes

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