Methyl iodide → (R)-(+)-Methyl 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl) oxy]benzoate

HRID 75980Notes

Reaction equation

HRID 75980 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:32]=[CH:31][C:12]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@@H:25]4[CH2:29][CH2:28][NH:27][C:26]4=[O:30])[CH:23]=3)[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=2)=[N:6][N:5]=1.[CH3:33]I>CN(C=O)C>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:10]=[CH:11][C:12]([O:13][C:14]3[CH:15]=[C:16]([CH:21]=[C:22]([O:24][C@@H:25]4[CH2:29][CH2:28][N:27]([CH3:33])[C:26]4=[O:30])[CH:23]=3)[C:17]([O:19][CH3:20])=[O:18])=[CH:31][CH:32]=2)=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86668096(R)-(+)-Methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((2-oxopyrrolidin-3-yl)oxy)benzoate2×

Product 1

HCID 86668095(R)-(+)-Methyl 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]-5-[(1-methyl-2-oxo-pyrrolidin-3-yl) oxy]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride suspension (0.16 g, 50%) was added to a stirring solution of (R)-(+)-Methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((2-oxopyrrolidin-3-yl)oxy)benzoate (1.5 g) (Intermediate 20) in dry DMF taken in a round bottomed flask fitted with anhydrous CaCl2 guard tube, at room temperature. The reaction mixture was stirred at the same temperature for 15 min. Methyl iodide (0.20 mL) was added and stirred till the reaction completed. The reaction mixture was quenched with ice-water, extracted with DCM. All organic layers were combined, washed with water, brine, dried over sodium sulphate, filtered and concentrated in vacuum to get the thick liquid product. The liquid was triturated with EtOAc:hexane to get the white solid product (1.2 g).

Workup

  1. customtaken in a round bottomed flask
  2. customfitted with anhydrous CaCl2 guard tube, at room temperature
  3. stirringstirred till the reaction
  4. customThe reaction mixture was quenched with ice-water
  5. extractionextracted with DCM
  6. washwashed with water, brine
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuum
  10. customto get the thick liquid product
  11. customThe liquid was triturated with EtOAc

Sources & evidence

ORD record
ord-37edd186f1a1499da2f8da731dff94ce
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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