Methyl iodide → 9-Hydroxy-6-methoxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehyde

HRID 236599Notes

Reaction equation

HRID 236599 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[O:19])[CH:5]=[C:6]2[C:14]=1[C:13](=[CH2:15])[C:12]1([OH:17])[O:16][N:7]2[CH2:8][CH:9]2[CH:11]1[NH:10]2.[H-].[Na+].[CH3:22]I>CN(C)C=O>[OH:17][C:12]12[O:16][N:7]([CH2:8][CH:9]3[CH:11]1[NH:10]3)[C:6]1[C:14](=[C:2]([O:1][CH3:22])[CH:3]=[C:4]([CH:18]=[O:19])[CH:5]=1)[C:13]2=[CH2:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 150517286,9-Dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehyde

Product 1

HCID 150517419-Hydroxy-6-methoxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-triene-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 6,9-dihydroxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (30 mg) in dimethylformamide (1.0 ml) was added a suspension of sodium hydride (60% in oil, 4.6 mg) in dimethylformamide (0.5 ml) in an ice-water bath. To this mixture was added a solution of methyl iodide (7.2 μl) in dimethylformamide (0.1 ml) in an ice-water bath. After stirring for 1 hour in an ice-water bath, the reaction mixture was evaporated to dryness in vacuo, and the residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (8:1, v/v) to afford 9-hydroxy-6-methoxy-8-methylene-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-triene-4-carbaldehyde (19 mg).

Workup

  1. customthe reaction mixture was evaporated to dryness in vacuo
  2. additionwas developed with a mixture of chloroform and methanol (8:1

Sources & evidence

ORD record
ord-390e9c5eaf0b4c7e91ff2c1a4f305080
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

Loading…