Methyl iodide → HCID 86675920, compound

HRID 572665Notes

Reaction equation

HRID 572665 reaction equation
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17]3[CH2:21][C@@H:20]([C@H:22]4[CH2:27][O:26][C@H:25]([C:28]([OH:30])=[O:29])[CH2:24][O:23]4)[O:19][N:18]=3)[CH:11]=2)=[O:9])=[CH:4][C:3]=1[O:33][CH3:34].[C:35](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([C:17]3[CH2:21][C@@H:20]([C@H:22]4[CH2:27][O:26][C@H:25]([C:28]([O:30][CH3:35])=[O:29])[CH2:24][O:23]4)[O:19][N:18]=3)[CH:11]=2)=[O:9])=[CH:4][C:3]=1[O:33][CH3:34]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86675921HCID 86675921, compound

Product 1

HCID 86675920HCID 86675920, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2S,5R)-5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxane-2-carboxylic acid (0.3 g, 0.632 mmol, Example #P.1) in DMF (2 mL) was added potassium carbonate (0.131 g, 0.948 mmol) followed by iodomethane (0.108 g, 0.759 mmol). The reaction mixture was stirred at RT for about 3 h. The reaction mixture was quenched with water (15 mL), the product separated as solids and collected by filtration, washed with water (10 mL) and dried under vacuum to obtain (2S,5R)-methyl 5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxane-2-carboxylate 0.270 g, (87%), ES-MS: m/z 489 (m+H)+, LC/MS (Table 1, method d) Rt=2.25 min.

Workup

  1. customThe reaction mixture was quenched with water (15 mL)
  2. customthe product separated as solids
  3. filtrationcollected by filtration
  4. washwashed with water (10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6cce3cb2bb934cbabd92c84031ca6c18
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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