Methyl iodide → (2S,5R)-1-tert-butyl 2-methyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-methyl-5,6-dihydropyridine-1,2(2H)-dicarboxylate

HRID 627088Notes

Reaction equation

HRID 627088 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]([OH:33])=[O:32])[CH:20]=[C:19]1[CH3:34])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].[C:35](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[C@H:21]([C:31]([O:33][CH3:35])=[O:32])[CH:20]=[C:19]1[CH3:34])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:7])=[O:8])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89851803(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid2×

Product 1

HCID 89851906(2S,5R)-1-tert-butyl 2-methyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-methyl-5,6-dihydropyridine-1,2(2H)-dicarboxylateYield 66.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid (Intermediate 19, 3 g, 6.03 mmol) and potassium carbonate (3.33 g, 24.12 mmol) in DMF (30 mL) at room temperature was added methyl iodide (0.454 mL, 7.24 mmol). After 1 hour the reaction mixture was diluted with ethyl acetate and washed three times with water. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-30% ethyl acetate/hexanes) afforded the desired product (2.060 g, 66.8%) as an off-white foam.

Workup

  1. washwashed three times with water
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec2a3962ab3445649d95a7a47ed5f363
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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