Triethylamine → methyl (S)-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate

HRID 350549Notes

Reaction equation

HRID 350549 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([O:23]C2C(F)=C(F)C(F)=C(F)C=2F)=O)[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].[NH2:35][C@@H:36]([CH3:49])[CH2:37][O:38][C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([NH:35][C@@H:36]([CH3:49])[CH2:37][O:38][C:39]2[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=2)=[O:23])[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

6

Reactant 3

HCID 8471TriethylamineHCID 23512249pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587805methyl (S)-4-(2-amino-1-propoxy)benzoate

Product 1

HCID 86611301methyl (S)-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoateYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (505 mg, 1.05 mmol), methyl (S)-4-(2-amino-1-propoxy)benzoate (220 mg, 1.05 mmol), and Et3N (0.220 mL, 1.58 mmol) in DMF (8 mL) was stirred at room temp for 3 hr. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine and dried over Na2SO4. After removal of the solvent, the residue was recrystallized from MeOH—CHCl3-n-hexane to give 290 mg (55%) methyl (S)-4-[2-[3-methoxy-4-[N′-(2-methylphenyl) ureido]phenylacetylamino]-1-propoxy]benzoate as a white crystalline powder. 1H-NMR (DMSO-d6) δ 1.18 (d, 3 H, J=6.8 Hz), 2.24 (s, 3 H), 3.36 (s, 2H), 3.80 (s, 3H), 3.82 (s, 3H), 3.93–4.03 (m, 2H), 4.09–4.14 (m, 1H), 6.75–8.57 (series of m, total 13 H).

Workup

  1. washwashed with 0.5 N HCl, brine
  2. dry with materialdried over Na2SO4
  3. customAfter removal of the solvent
  4. customthe residue was recrystallized from MeOH—CHCl3-n-hexane

Sources & evidence

ORD record
ord-03cda43e8e3043fa8030ac87b442230d
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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