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

HRID 350552Notes

Reaction equation

HRID 350552 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].[Cl:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH2:47][C@@H:48]([NH2:50])[CH3:49])[C:39]([O:41][CH3:42])=[O:40]>CN(C=O)C.CCOC(C)=O>[Cl:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[O:46][CH2:47][C@@H:48]([NH:50][C:21](=[O:23])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:49])[C:39]([O:41][CH3:42])=[O:40]

Participants

5

Reactant 2

HCID 23512249pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587793methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate

Product 1

HCID 86587794methyl (S)-3-chloro-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoateYield 69.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (513 mg, 1.07 mmol), methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate (260 mg, 1.07 mmol) and Et3 N (220 μl, 1.58 mmol) in DMF (10 mL) was stirred at room temp overnight. The mixture was diluted with EtOAc and the solution was washed with sat. NaHCO3, dried over Na2SO4, and evaporated. The residue was recrystallized from MeOH—CHCl3-EtOAc-n-hexane to give 400 mg (69%) methyl (S)-3-chloro-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as pale brown crystalline powder. 1H-NMR (DMSO-d6) δ 1.21 (d, 3 H, J=6.4 Hz), 2.24 (s, 3 H), 3.37 (s, 2 H), 3.82(s, 3 H), 3.83 (s, 3 H), 4.04–4.12 (m, 3 H), 6.75–6.77 (m, 1 H), 6.91–6.95 (m, 2 H), 7.11–7.17 (m, 2 H), 7.29–7.31 (m, 1 H), 7.78–7.99 (m, 4 H), 8.12–8.13 (m, 1H), 8.46 (s, 1 H), 8.55 (s, 1 H).

Workup

  1. washthe solution was washed with sat. NaHCO3
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was recrystallized from MeOH—CHCl3-EtOAc-n-hexane

Sources & evidence

ORD record
ord-79f60a2c70cc455988c79736508b65cd
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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