Methyl iodide → Racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide

HRID 661900Notes

Reaction equation

HRID 661900 reaction equation
[Br:1][C:2]1[C:3]([CH3:27])=[C:4]([NH:8][C:9](=[O:26])[CH:10]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][CH2:12][S:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.[I:28][CH3:29]>C(Cl)Cl>[I-:28].[CH2:18]([O:17][C:16]([NH:15][CH:10]([C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[CH3:27])=[O:26])[CH2:11][CH2:12][S+:13]([CH3:29])[CH3:14])=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 66606795Racemic benzyl 1-(3-bromo-2-methylphenylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate

Product 1

HCID 87071307Racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodideYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Step 2 A mixture of racemic benzyl 1-(3-bromo-2-methylphenylamino)-4-(methylthio)-1-oxobutan-2-ylcarbamate (1.31 g, 2.90 mmol) and DCM (4 mL) was diluted with iodomethane (7.5 mL, 120 mmol) and the mixture was stirred at rt. After 24.5 h, the mixture (a solution with an insoluble reddish oil) was concentrated under vacuum. The residue was treated three times with DCM and concentrated under vacuum to provide racemic (3-(benzyloxycarbonylamino)-4-(3-bromo-2-methylphenylamino)-4-oxobutyl)dimethylsulfonium iodide as an orange-yellow glassy foam (1.75 g, 97%). 1H NMR (400 MHz, chloroform-d) 69.16 (1H, br. s.), 7.28-7.46 (7H, m), 6.99 (1H, t, J=8.0 Hz), 6.71 (1H, d, J=6.8 Hz), 5.11 (2H, s), 4.84 (1H, br. s.), 3.75 (1H, br. s.), 3.54 (1H, br. s.), 3.14 (3H, br. s.), 2.96 (3H, s), 2.75 (1H, br. s.), 2.33-2.41 (1H, m), 2.30 (3H, br. s.). Mass spectrum m/z 465, 467 (M)+.

Workup

  1. concentrationthe mixture (a solution with an insoluble reddish oil) was concentrated under vacuum
  2. additionThe residue was treated three times with DCM
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b7173c514b6e46f68940b59ffd194835
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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