1,1-Dichloroethane → 3-{4-[1-(4-Butoxyphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]-benzoylamino}propionic Acid

HRID 1633969Notes

Reaction equation

HRID 1633969 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.C(OC1C=CC([NH:26][CH2:27][C:28]2[CH:41]=[CH:40][C:31]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:30][CH:29]=2)=CC=1)CCC.Cl[CH:43](Cl)[CH3:44]>>[CH2:32]([O:33][C:43]1[CH:44]=[CH:40][C:41]([CH:27]([NH:26][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:9][CH:8]=2)=[O:12])[C:28]2[CH:29]=[CH:30][C:31]([C:32]([NH:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[O:33])=[CH:40][CH:41]=2)=[CH:28][CH:27]=1)[CH2:31][CH2:30][CH3:29]

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 225020713-{4-[(4-Butoxyphenylamino)methyl]benzoylamino}propionic Acid

Product 1

HCID 225020583-{4-[1-(4-Butoxyphenyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]-benzoylamino}propionic Acid

Conditions

Temperature
25 °C

Procedure

200 μmol 4-trifluoromethoxyphenylisocyanate dissolved in 500 μL dichloroethane was added to the above resin bound 3-{4-[(4-butoxyphenylamino)methyl]benzoylamino}propionic acid (50 mg). Shaking the mixture 5 hours at 25° C. followed by filtration and washing of the resin with 2×1 mL dichloromethane, 4×1 mL DMF, 2×1 mL H2O, 3×1 mL THF and 3×1 dichloromethane afforded the resin bound title compound.

Workup

  1. additionwas added to the above resin
  2. filtrationfollowed by filtration
  3. washwashing of the resin with 2×1 mL dichloromethane, 4×1 mL DMF, 2×1 mL H2O, 3×1 mL THF and 3×1 dichloromethane
  4. customafforded the resin

Sources & evidence

ORD record
ord-8c2eeeae027d4e4497a770c26397a48d
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

Loading…