Methanol → HCID 59775598, compound

HRID 557465Notes

Reaction equation

HRID 557465 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[CH3:18][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27723423-amino-3-(3-iodophenyl)propanoic acid

Product 1

HCID 59775598HCID 59775598, compoundYield 95%

Procedure

To a suspension of (±)-3-Amino-3-(3-iodo-phenyl)-propionic acid (3.1 g, 10.6 mmol) in methanol was added thionyl chloride (0.95 mL, 12.7 mmol) and the reaction was stirred at room temperature overnight. Concentration followed by trituration with ether gives a white solid. The solid is filtered, washed with ether and dried to afford the desired product (3.5 g, 10 mmol, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.79 (br, 2H), 8.01 (s, 1H), 7.74 (d, J=8.1 Hz, 1H). 7.57 (d, J=7.8 Hz, 1H), 7.21 (dd, J=8.1, 7.8 Hz, 1H), 4.56 (br, 1H), 3.54 (s, 3H), 3.23-3.17 (m, 1H), 3.04-2.98 (m, 1H).

Workup

  1. concentrationConcentration
  2. customgives a white solid
  3. filtrationThe solid is filtered
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-ac3dc423ba244e298f2c0f526680be5a
Source dataset
uspto-grants-2011_11
Patent number
US08058449B2

Reaction notes

Loading…