Dimethylformamide → (S)-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoic acid

HRID 354489Notes

Reaction equation

HRID 354489 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:13][CH:12]=1.[NH2:33][C@@H:34]([CH3:47])[CH2:35][O:36][C:37]1[CH:46]=[CH:45][C:40]([C:41]([O:43]C)=[O:42])=[CH:39][CH:38]=1.CCN(CC)CC.CN([CH:58]=[O:59])C>CCOC(C)=O>[CH3:58][O:59][C:16]1[CH:15]=[C:14]([CH2:17][C:18]([NH:33][C@@H:34]([CH3:47])[CH2:35][O:36][C:37]2[CH:46]=[CH:45][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)=[O:20])[CH:13]=[CH:12][C:11]=1[NH:10][C:9]([NH:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 23512272pentafluorophenyl 4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587805methyl (S)-4-(2-amino-1-propoxy)benzoate

Product 1

HCID 60092117(S)-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoic acidYield 36%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pentafluorophenyl 4-[N′-(2-methylphenyl)ureido]phenylacetate (560 mg, 1.24 mmol), methyl (S)-4-(2-amino-1-propoxy)benzoate (260 mg, 1.24 mmol), Et3N (0.260 mL, 1.87 mmol) in DMF (8 mL) was stirred at room temp for 3 hr. The mixture was diluted with EtOAc and the solution was washed with 0.5 N HCl, brine, and dried over Na2SO4. After removal of the solvent, the residue was purified by recrystallization from MeOH—CHCl3-n-hexane to give 210 mg (36%) (S)-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoic acid as a white crystalline powder. 1H-NMR (DMSO-d6) δ1.17 (d, 3 H, J=6.8 Hz), 2.24 (s, 3 H), 3.32 (s, 2 H), 3.81 (s, 3 H), 3.92-4.03 (m, 2 H), 4.08-4.15 (m, 1 H), 6.92-6.95 (m, 1 H), 7.04-7.06 (m, 2 H), 7.12-7.18 (m, 4 H), 7.35-7.39 (m, 2 H), 7.83-7.85 (m, 1 H), 7.89-7.92 (m, 3 H), 8.12-8.14 (m, 1 H), 8.97 (s, 1 H).

Workup

  1. washthe solution was washed with 0.5 N HCl, brine
  2. dry with materialdried over Na2SO4
  3. customAfter removal of the solvent
  4. customthe residue was purified by recrystallization from MeOH—CHCl3-n-hexane

Sources & evidence

ORD record
ord-b495b5d356074ee8a3157b322aaf7fca
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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