Potassium Carbonate → HCID 9843222, compound

HRID 2219244Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([S:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8].[SH:18][C:19]1[O:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[S:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([S:16][CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a DMF (2 ml) solution of this amide (159 mg, 0.5 mmol) and 2-mercaptobenzoxazole (83 mg, 0.55 mmol) were added 18-crown-6 (13 mg, 0.05 mmol) and potassium carbonate (83 mg, 0.6 mmol). and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 20 g, eluent-hexane:ethyl acetate=5:2→2:1) to obtain 156 g (yield 81%) of a desired compound as a colorless needle crystal.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
distillationSubsequently, the solvent was distilled off
customthe resulting crude product was purified through silica gel chromatography (silica gel 20 g, eluent-hexane:ethyl acetate=5:2→2:1)

Sources & evidence

ORD record: ord-a157e7601a92488b866d9fef7a5cb9b6
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414066B2

Reaction notes

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