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

HRID 354500Notes

Reaction equation

HRID 354500 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].[N+:35]([C:38]1[CH:39]=[C:40]([CH:45]=[CH:46][C:47]=1[O:48][CH2:49][C@@H:50]([NH2:52])[CH3:51])[C:41]([O:43][CH3:44])=[O:42])([O-:37])=[O:36].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[N+:35]([C:38]1[CH:39]=[C:40]([CH:45]=[CH:46][C:47]=1[O:48][CH2:49][C@@H:50]([NH:52][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)[CH3:51])[C:41]([O:43][CH3:44])=[O:42])([O-:37])=[O:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23512249pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 69334207methyl(S)-3-nitro-4-(2-amino-1-propoxy)benzoate

Product 1

HCID 86587800methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenyl acetylamino]-1-propoxy]benzoateYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (591 mg, 1.23 mmol), methyl (S)-3-nitro-4-(2-amino-1-propoxy)benzoate (313 mg, 1.23 mmol), and Et3N (257 mL, 1.84 mmol) in DMF (5 mL) was stirred at room temp for 2 days. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent to give 310 mg (46%) methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as a gum. 1H-NMR (CDCl3) δ1.28 (d, 3H, J=6.8 Hz), 2.31 (s, 3 H), 3.49 (s, 2 H, 3.71 (s, 3 H), 3.92 (s, 3 H), 4.14-4.16 (m, 2 H), 4.38-4.41 (m, 1 H), 5.88-5.90 (m, 1 H), 6.49 (s, 1 H), 6.70-6.71 (m, 1 H), 6.77-6.79 (m, 1 H), 7.05-7.30 (m, 4 H), 7.55-7.57 (m, 1 H), 8.02-8.06 (m, 2 H), 8.16-8.19 (m, 1 H), 8.51-8.52 (m, 1 H); MS (FAB) m/z 551 (M++1).

Workup

  1. washwashed with 0.5 N HCl, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent

Sources & evidence

ORD record
ord-75b7546bb73642edb4d8f8c99d53acec
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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