Water → pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetate

HRID 350345Notes

Reaction equation

HRID 350345 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].FC(F)(F)C(O[C:29]1[C:34]([F:35])=[C:33]([F:36])[C:32]([F:37])=[C:31]([F:38])[C:30]=1[F:39])=O.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([O:23][C:29]2[C:30]([F:39])=[C:31]([F:38])[C:32]([F:37])=[C:33]([F:36])[C:34]=2[F:35])=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acid

Product 1

HCID 23512249pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (1.30 g, 4.136 mmol), Et3 N (0.63 mL, 4.549 mmol) in DMF (20 mL) was added pentafluorophenyl trifluoroacetate at 0° C. The resulting mixture was stirred at room temp for 1 hr. The mixture was poured into water (60 mL) and precipitate was collected with suction. The crude solid was washed with 0.1 N HCl, H2O, n-hexane, and dried at 40° C. to afford 1.91 g (96%) pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl) ureido]phenylacetate as a pale brownish crystalline powder. IR (KBr) 1785, 1224, 1216 cm−1; 1H-NMR (400 MHz, CDCl3) δ 2.29 (s, 3H), 3.76 (s, 3H), 3.90 (s, 2H), 6.49 (s, 1H), 6.81 (d, J=1.5 Hz, 1H), 6.91 (dd, J=1.5, 8.3 Hz, 1H), 7.15 (t, J=7.3 Hz, 3H), 7.24 (m, 1H), 7.50 (d, J=7.8 Hz, 1H), 8.17 (d, J=7.8 Hz, 1H); MS (FAB) m/z 481 (M++1); Anal. Calcd for C30H33N3O5S.1/4H2O: C, 57.51; H, 3.57; N, 5.83. Found: C, 57.40; H, 3.75; N, 5:68.

Workup

  1. customwas collected with suction
  2. washThe crude solid was washed with 0.1 N HCl, H2O, n-hexane
  3. customdried at 40° C.

Sources & evidence

ORD record
ord-1ffbfa113e2644ffb02d09568c7bd95f
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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