Triethylamine → dimethyl (S)-4-[1-[3-methoxy-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]phthalate

HRID 354290Notes

Reaction equation

HRID 354290 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[C:11](=[CH:16][CH:17]=1)[C:12]([O:14][CH3:15])=[O:13].C[O:23][C:24]1[CH:25]=[C:26](CC(O)=O)[CH:27]=[CH:28][C:29]=1[NH:30][C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:40])=[O:32].CCN(CC)CC.C[CH2:53][O:54][C:55]([CH3:57])=O>CN(C=O)C>[CH3:53][O:54][C:55]1[CH:57]=[C:28]([CH:29]([NH:30][C:31]([NH:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])=[O:32])[C:24]([N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[CH2:6][O:7][C:8]2[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[C:11](=[CH:16][CH:17]=2)[C:12]([O:14][CH3:15])=[O:13])=[O:23])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 86595075dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate

Product 1

HCID 86759471dimethyl (S)-4-[1-[3-methoxy-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]phthalateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of dimethyl (S)-4-(2-pyrrolidinylmethoxy)phthalate (212 mg, 0.72 mmol) in DMF (8 mL) was added pentafluorophenyl ester of the 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (346 mg, 0.72 mmol) and Et3N (120 ml, 0.86 mmol), and the mixture was stirred overnight. The resulting mixture was diluted with EtOAc, washed with 1 N HCl, sat. NaHCO3, brine, and dried over MgSO4. The solvent was evaporated off in vacuo to give 413 mg (97%) dimethyl (S)-4-[1-[3-methoxy-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]phthalate as an oil. 1H-NMR (CDCl3) δ1.92-2.12 (m, 4 H), 2.29 (br s, 3 H), 3.51-3.64 (m, 7 H), 3.87 (s, 3 H), 3.89 (s, 3 H), 4.10-4.19 (m, 2 H), 4.44 (m, 1 H), 6.73-8.02 (series of m, total 12 H).

Workup

  1. washwashed with 1 N HCl, sat. NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated off in vacuo

Sources & evidence

ORD record
ord-abca74fcf51d4b4597259b999732e674
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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