Methyl iodide → HCID 86660145, compound

HRID 523922Notes

Reaction equation

[C:1]([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:24]1[CH:29]=[C:28]([OH:30])[CH:27]=[CH:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:8].CI.CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:24]1[CH:29]=[C:28]([O:30][CH3:1])[CH:27]=[CH:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:8]

Participants

Conditions

Temperature: 70 °C

Procedure

K2CO3 (15 mg, 0.11 mmol) was added to II (25 mg, 0.073 mmol) in DMF (2 mL) at rt under Ar(g). After 15 min CH3I (5 μL, 0.073 mmol) was added and the reaction was stirred at 70° C. for 22 h. Brine (30 mL) and EtOAc (30 mL) were added, then the phases were separated, and the aqueous phase was extracted with EtOAc (2×20 mL). The organic phases were combined then dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (60:40) to furnish III as a colourless oil (10 mg, 40%).

Workup

customthe phases were separated
extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
dry with materialThe organic phases were combined then dried over MgSO4
filtrationfiltered
customsubsequently evaporated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography
washeluting with hexane/EtOAc (60:40)

Sources & evidence

ORD record: ord-1123df0c4d9e4ff188faf2a8f72d8a88
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340503B2

Reaction notes

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