N-Iodosuccinimide → Ethyl 5-((tert-butoxycarbonyl)amino)-2-iodothiazole-4-carboxylate

HRID 2060630Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][CH:12]=[N:11][C:10]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:19]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([I:19])=[N:11][C:10]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 5-[(tert-butoxycarbonyl)amino]-1,3-thiazole-4-carboxylate (10 g, 36.7 mmol) in DMF (122 ml) was added N-iodosuccinimide (20 g, 88.9 mmol). The mixture was stirred for 36 hrs at 60° C. One additional equivalent of N-iodosuccinimide (1.2 g) was added and the mixture was stirred at 60° C. for 18 hrs. The reaction was then cooled to room temperature and concentrated to one-third its volume in vacuo. The resulting mixture was partitioned between water and ethyl acetate. The aqueous layer was further extracted once with dichloromethane. The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo, and purified via flash chromatography (silica, 0-20% ethyl acetate/hexanes) to afford the title compound. LRMS (APCI) calc'd for (C11H16IN2O4S) [M+H]+, 399.0; found 398.9.

Workup

stirringthe mixture was stirred at 60° C. for 18 hrs
temperatureThe reaction was then cooled to room temperature
concentrationconcentrated to one-third its volume in vacuo
customThe resulting mixture was partitioned between water and ethyl acetate
extractionThe aqueous layer was further extracted once with dichloromethane
dry with materialThe combined organics were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
custompurified via flash chromatography (silica, 0-20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-87db9e196ea541be86ef2fe76eff64f7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278335B2

Reaction notes

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