N-Iodosuccinimide → HCID 54687146, compound

HRID 2111512Notes

Reaction equation

[CH3:1][N:2]([C@@H:4]1[C:23]([OH:24])=[C:22]([C:25]([NH2:27])=[O:26])[C:20](=[O:21])[C@:19]2([OH:28])[C@H:5]1[CH2:6][C@H:7]1[C:17](=[C:18]2[OH:29])[C:15](=[O:16])[C:14]2[C:13]([OH:30])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)[CH3:3].[I:31]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[CH3:3][N:2]([C@@H:4]1[C:23](=[O:24])[C:22]([C:25]([NH2:27])=[O:26])=[C:20]([OH:21])[C@:19]2([OH:28])[C@H:5]1[CH2:6][C@H:7]1[C:17]([C:18]2=[O:29])=[C:15]([OH:16])[C:14]2[C:9](=[C:10]([I:31])[CH:11]=[CH:12][C:13]=2[OH:30])[CH2:8]1)[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

Five grams of sancycline was dissolved in 85 mL of concentrated sulfuric acid that was cooled to 0° C. (on ice). N-iodosuccinimide (NIS) was added to the reaction in 300 mg portions every 15 minutes and reacted for 5 hours. The reaction is removed from the ice bath. The mixture, analyzed by HPLC or TLC, show the product of D-ring iodotetracyclines. After the reaction was complete, the sulfuric acid was dripped slowly 1 L of ice water and extracted 7 times with 300 mL of n-butanol. The solvent was removed in vacuo to produce a mixture of three products. The 7-iodo regioisomer, 9-regioisomer and 7,9-diiodosancycline derivative of sancycline were purified by preparative HPLC chromatography or by methods known in the art.

Workup

customreacted for 5 hours
customThe reaction is removed from the ice bath
extractionextracted 7 times with 300 mL of n-butanol
customThe solvent was removed in vacuo
customto produce
additiona mixture of three products
customThe 7-iodo regioisomer, 9-regioisomer and 7,9-diiodosancycline derivative of sancycline were purified by preparative HPLC chromatography or by methods

Sources & evidence

ORD record: ord-4a9853ca90a843c3a345786b0447ba81
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521437B2

Reaction notes

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