Methyl iodide → HCID 86668094, compound

HRID 75976Notes

Reaction equation

HRID 75976 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 68106907(S)-(-)-methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((2-oxopyrrolidin-3-yl)oxy)benzoate2×

Product 1

HCID 86668094HCID 86668094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride suspension (0.71 g, 50%) was added to a stirring solution of (S)-(−)-methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((2-oxopyrrolidin-3-yl)oxy)benzoate (5.5 g) (Intermediate 15) 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 (0.91 mL) was added and stirred till the reaction completion. 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 vaccuo to get the thick liquid product. The liquid was triturated with EtOAc:hexane to get the white solid product (5.3 g).

Workup

  1. customtaken in a round bottomed flask
  2. customfitted with anhydrous CaCl2 guard tube at room temperature
  3. stirringstirred till the reaction completion
  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 vaccuo
  10. customto get the thick liquid product
  11. customThe liquid was triturated with EtOAc

Sources & evidence

ORD record
ord-bdbbae6a1b154a70b70bdd29adcaadac
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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