Methyl iodide → HCID 68772517, compound

HRID 1174956Notes

Reaction equation

HRID 1174956 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].IC.[C:31](OCC)(=O)[CH3:32]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][N:14]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:31][CH3:32])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 57771757HCID 57771757, compound

Product 1

HCID 68772517HCID 68772517, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

Dissolve 3-[(6-nitro-benzothiazol-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (5.55 g, 14.7 mmol) in DMF (30 mL) and cool to 5° C. Add 60% NaH in mineral oil (1.12 g, 16.13 mmol) and stir for 5 min. Add iodomethane (6.0 mL, 74 mmol) and stir at 5° C. for 30 min. Quench the reaction with water and dilute with ethyl acetate. Wash the organic layer with water (5×20 mL), then wash with brine. Collect the organic layer, dry over Na2SO4, filter, and concentrate in vacuo. Chromatograph (silica gel, eluting with 20-60% Ethyl acetate:Hexane) to yield 1.96 g (34%) of the title compound. mass spectrum (ion-spray): (m/z)=393.3 (M+1).

Workup

  1. customQuench
  2. customthe reaction with water
  3. washWash the organic layer with water (5×20 mL)
  4. washwash with brine
  5. customCollect the organic layer
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. washChromatograph (silica gel, eluting with 20-60% Ethyl acetate:Hexane)

Sources & evidence

ORD record
ord-a1573ab42ba64ac39b2a6dce2ad4ce4b
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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