Iodoethane → HCID 91754469, compound

HRID 1472942Notes

Reaction equation

HRID 1472942 reaction equation
[C:1]([NH:4][CH:5]([CH2:9][S:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH2:20](N(CC)CC)[CH3:21].ICC>O>[C:1]([NH:4][C@@H:5]([CH2:9][S:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)[C:6]([O:8][CH2:20][CH3:21])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 118014508HCID 118014508, compound

Product 1

HCID 91754469HCID 91754469, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-acetylamino-3-(4-methyl-benzoylsulfanyl)-propionic acid (1.1 g, 3.91 mmol) and triethylamine (0.68 mL, 4.89 mmol) N,N-dimethylformamide (5 mL) was added iodoethane (0.39 mL, 4.89 mmol) and the resulting solution was stirred at ambient temperature for 18 hours. The reaction mixture was added slowly to water (50 mL) with rapid stirring. After stirring for 2 hours, the resulting slurry was filtered and the solid was rinsed with water and dried under vacuum to give the product as a white solid (780 mg, 60%). 1H NMR (300 MHz, DMSO) δ=8.47 (d, J=7.9 Hz, 1H), 7.81 (s, 1H), 7.80-7.78 (m, 1H), 7.35 (d, J=7.6 Hz, 2H), 4.46 (dt, J=5.3, 8.1 Hz, 1H), 4.09 (q, J=6.8 Hz, 2H), 3.50 (dd, J=5.4, 13.6 Hz, 1H), 3.24 (dd, J=8.2, 13.8 Hz, 1H), 2.37 (s, 3H), 1.83 (s, 3H), 1.16 (t, J=7.0 Hz, 3H). MS (ESI) m/z 310 (M+1)+.

Workup

  1. stirringAfter stirring for 2 hours
  2. filtrationthe resulting slurry was filtered
  3. washthe solid was rinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-def72550c8244e1d808e2fe03fe629cc
Source dataset
uspto-grants-2015_04
Patent number
US09012674B1

Reaction notes

Loading…