HCID 178418287, compound → HCID 178439833, compound

HRID 46158Notes

Reaction equation

[OH:1][C@H:2]1[CH2:7][C@H:6]2[CH2:8][C@@H:3]1[CH2:4][C@@H:5]2[NH:9][C:10]1[S:11][C:12]([CH:17]([CH3:19])[CH3:18])([CH3:16])[C:13](=[O:15])[N:14]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH:17]([C:12]1([CH3:16])[S:11][C:10]([NH:9][C@H:5]2[CH2:4][C@H:3]3[CH2:8][C@@H:6]2[CH2:7][C:2]3=[O:1])=[N:14][C:13]1=[O:15])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Silica gel 60 (particle size, 0.040-0.063 mm, CAS # 63231-67-4, from EMD Chemical Inc., 2.4 g) was added to a solution of 2-((1R,2S,4R,5S)-5-hydroxybicyclo[2.2.1]heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5H)-one (0.709 g, 2.51 mmol) in anhydrous dichloromethane (40 mL). The mixture was cooled to 0° C. Pyridinium chlorochromate (1.08 g, 5.02 mmol) was added, and the reaction mixture was gradually warmed to ambient temperature and stirred overnight. The mixture was diluted with dichloromethane, and filtered through a pad of Celite. The solvents were removed in vacuo and the residue was purified by flash column chromatography (0 to 100% of EtOAc in hexanes) to give the title compound as a tan solid.

Workup

temperaturethe reaction mixture was gradually warmed to ambient temperature
filtrationfiltered through a pad of Celite
customThe solvents were removed in vacuo
customthe residue was purified by flash column chromatography (0 to 100% of EtOAc in hexanes)

Sources & evidence

ORD record: ord-92e6da4847d64cb3bb25028a48ba8cb8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541592B2

Reaction notes

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