Hydrochloric Acid → 4-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoic acid

HRID 350548

反応式

HRID 350548 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:38]=[CH:37][C:31]([C:32]([O:34]CC)=[O:33])=[CH:30][CH:29]=2)[CH3:24])=[O:22])[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].[OH-].[Na+].Cl>C1COCC1.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:23]([CH2:25][CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[CH:37][CH:38]=2)[CH3:24])=[O:22])[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23512235HCID 23512235、化合物

生成物 1

HCID 235123274-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoic acid収率 28%

試薬・触媒・溶媒 2

HCID 56841950ICE protocol 1触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of ethyl 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenyl acetyl-N-methylamino]-1propyl]benzoate (500 mg, 0.966 mmol) in THF (8 mL) was added 0.25 N NaOH (8 mL), and the mixture was heated under reflux overnight. The resulting solution was poured into ice-1 N HCl (100 mL) and the solid was collected with suction. The solid was dissolved in CHCl3 (100 mL) and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica gel with CHCl3-MeOH (10:1 to 5:1, v/v) to give 131 mg (28%) 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoic acid 269 as a pale yellow amorphous solid. 1H-NMR (DMSO-d6) δ 1.68–1.80 (m, 2 H), 2.24 (s, 3 H), 2.57 (m, 2 H), 2.81 and 2.97 (s, each, total 3 H), 3.33 (m, 2 H), 3.57–3.61 (m, 2 H), 3.84 (s, 3 H), 6.71 (dd, J=29.8, 8.3 Hz, 1H), 6.87 (d, J=11.2 Hz, 1H), 6.93 (t, J=7.3 Hz, 1H), 7.15 (m, 2H), 7.28 (m, 2 H), 7.79 (d, J=8.3 Hz, 1 H), 7.84–7.87 (m, 2 H), 8.02 (d, J=8.3 Hz, 1 H), 8.49 (d, J=7.3 Hz, 1 H), 8.58 (d, J=4.9 Hz, 1 H); MS (FAB) m/z 490 (M++1); Anal. Calcd for C28H31N3O5.1/2H2O: C, 67.45; H, 6.47; N, 8.43. Found: C, 67.27; H, 6.51; N, 8.02.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customthe solid was collected with suction
  4. dissolutionThe solid was dissolved in CHCl3 (100 mL)
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent
  7. customthe residue was chromatographed on silica gel with CHCl3-MeOH (10:1 to 5:1

出典と根拠

ORDレコード
ord-1195b2357c544f3ea21da6a1fe679be4
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

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