Methyl iodide → HCID 131721119, compound

HRID 362699Notes

Reaction equation

HRID 362699 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10](=[O:31])[C@@H:11]2[C@@H:15]([CH2:16][CH3:17])[CH2:14][CH2:13][N:12]2[CH:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:19]2[CH2:23][CH2:22][CH2:21][NH:20]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:35]>CN(C=O)C>[CH3:35][N:9]([CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:10](=[O:31])[C@@H:11]1[C@@H:15]([CH2:16][CH3:17])[CH2:14][CH2:13][N:12]1[CH:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131721118HCID 131721118, compound

Product 1

HCID 131721119HCID 131721119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-[(t-Butyloxycarbonyl)-pyrrolidin-2(S)-ylmethyl]-3(S)-ethyl-proline-N-(3-chlorophenylmethyl) amide (0.175 g, 0.39 mmol) was dissolved in dry DMF (4 mL) with stirring at 0° C. under Ar, treated with NaH (60% dispersion in mineral oil, 0.023 g, 0.58 mmol), and after 15 minutes treated with iodomethane (0.029 mL, 0.47 mmol). The reaction mixture was stirred at 25° C. for 2 h, then evaporated to dryness and partitioned between EtOAc and aqueous saturated NaHCO3 solution. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to dryness to give the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 25° C. for 2 h
  2. customevaporated to dryness
  3. custompartitioned between EtOAc and aqueous saturated NaHCO3 solution
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7c022b5070f34edeb77bd003d987765f
Source dataset
uspto-grants-1999_02
Patent number
US05869682

Reaction notes

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