Methyl iodide → HCID 71133843, compound

HRID 1523117Notes

Reaction equation

HRID 1523117 reaction equation
[C:1]([CH2:8][N:9]1[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17][N:16]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:31]I>C(Cl)(Cl)Cl>[C:24]([CH2:23][N:16]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10][N:9]([CH2:8][C:1]([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2])[CH2:22][CH2:21][CH2:20][N:19]([CH3:31])[CH2:18][CH2:17]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 68106176HCID 68106176, compound

Product 1

HCID 71133843HCID 71133843, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of compound (5) (2.33 g, 5.43 mmol) in dry chloroform (50 ml) was added methyl iodide (6.78 ml, 15.43 g, 108.72 mmol). After stirring at an ambient temperature for 24 hours, the solvent was removed from the reaction mixture under reduced pressure. The residue was purified via column chromatography on silica using chloroform/isopropyl amine (20:2) as an eluent, to obtain compound (31) as a clear oil (2.41 g, 84% yield). 1H NMR (500 MHz, CDCl3): δ 3.27-3.25 (dd, 4H), 2.84-2.43 (m, 16H), 2.16 (s, 3H), 1.73-1.59 (m, 4H), 1.45 (s, 18H); 13C NMR (125 MHz, CDCl3): δ 170.94, 170.68, 80.57, 55.99, 55.93, 54.80, 53.77, 53.40, 52.26, 50.11, 48.34, 47.41, 47.17, 41.88, 28.18, 25.59, 25.00; HRMS (FAB) calculated for C23H47N4O4: 443.3597 [(M+H)+], measured value: 443.3600 [(M+H)+].

Workup

  1. customthe solvent was removed from the reaction mixture under reduced pressure
  2. customThe residue was purified via column chromatography on silica

Sources & evidence

ORD record
ord-1c049400e62b48438fd941154e1de703
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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