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

HRID 1811081Notes

Reaction equation

HRID 1811081 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) δ9.16 (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-9b21edc0fcf74f899316754b436141c6
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

Loading…