Sodium hydride → HCID 22730180, compound

HRID 2356144Notes

Reaction equation

[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C1OCCOCCOCCOCCOC1.[H-].[Na+].Br[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)=[C:36]([O:50][CH3:51])[CH:35]=1>CN(C=O)C.O>[CH3:51][O:50][C:36]1[CH:35]=[C:34]([CH2:33][N:7]2[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][C:2]2=[O:1])[CH:39]=[CH:38][C:37]=1[C:40]1[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of Example 500B (328 mg, 1.64 mmol) in DMF (4 mL) at room temperature was treated with 15-crown-5 (361 mg, 1.64 mmol) and 60% sodium hydride in mineral oil (66 mg, 1.64 mmol). The mixture was treated with a solution of Example 500C (500 mg, 1.49 mmol) in DMF (2 mL), heated to 60° C. for 16 hours, cooled to room temperature, treated with water (20 mL), and extracted three times with ethyl acetate (50 mL). The combined extracts were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes to provide the desired product.

Workup

temperaturecooled to room temperature
extractionextracted three times with ethyl acetate (50 mL)
washThe combined extracts were washed with brine (10 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash column chromatography on silica gel with 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record: ord-be3747ac5ddf47fca90a7da868fbb5c0
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754886B2

Reaction notes

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