Methyl iodide → HCID 131734367, compound

HRID 1507197Notes

Reaction equation

HRID 1507197 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([CH2:23][CH2:24][S:25][CH3:26])[C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:28][I:29]>>[I-:29].[C:1]([O:5][C:6]([NH:7][C@@H:8]([C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=1)=[O:10])[CH2:23][CH2:24][S+:25]([CH3:28])[CH3:26])=[O:27])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 118217189HCID 118217189, compound

Product 1

HCID 131734367HCID 131734367, compound

Procedure

A mixture of (R)-tert-butyl(1-((3,4-dimethoxybenzyl)amino)-4-(methylthio)-1-oxobutan-2-yl)carbamate (2 g, 5 mmol) and methyl iodide (24 ml, 381 mmol) was stirred at RT for 48 hrs. The solvent was then evaporated off and the residue was triturated with ether and dried under high vacuum. Yield 2 g. LCMS (Method J) RT 0.64 min, m/z 413.1 (M+); 1H NMR (400 MHz, chloroform-d) δ 1.40 (s, 9H), 2.08-2.21 (br s, 1H), 2.55-2.70 (br s, 1H), 3.06 (s, 3H), 3.23 (s, 3H), 3.70-3.80 (br s, 1H), 3.85 (s, 3H), 3.89 (s, 3H), 4.34 (m, 2H), 4.45-4.55 (br s, 1H), 6.07 (d, J=6.8, 1H) 6.79 (d, J=8, 1H), 6.91 (m, 1H), 7.26 (s, 1H), 8.16 (s, 1H). The crude reaction product was used directly in the next step.

Workup

  1. customThe solvent was then evaporated off
  2. customthe residue was triturated with ether
  3. customdried under high vacuum
  4. customLCMS (Method J) RT 0.64 min, m/z 413.1 (M+)
  5. customThe crude reaction product

Sources & evidence

ORD record
ord-847529c3d85c4e1d8afc898259267a6d
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

Loading…