Water → HCID 68928964, compound

HRID 1260972Notes

Reaction equation

HRID 1260972 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([N:13]2[CH2:18][CH2:17][C@@H:16]([N:19]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[O:22])[CH3:20])[C@H:15]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[CH2:14]2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:38]C(C)([O-])C.[Na+].CI.O>CN(C=O)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]([CH3:38])[C:11]([N:13]2[CH2:18][CH2:17][C@@H:16]([N:19]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[O:22])[CH3:20])[C@H:15]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[CH2:14]2)=[O:12])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23676156Sodium t-butoxideHCID 68930226HCID 68930226, compound

Product 1

HCID 68928964HCID 68928964, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 459 (100 mg) in DMF (3 mL) was added sodium tert-butoxide (25.3 mg) at 0° C., and the mixture was stirred for 5 min. Then, methyl iodide (16.5 μL) was added, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 0→12% methanol/ethyl acetate) to give the title compound (55 mg, 54%) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hr
  2. extractionthe resultant product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 0→12% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-e0a7741688a942499071c2f3080aa087
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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