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

HRID 354486

반응식

HRID 354486 반응식
[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]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23512235HCID 23512235, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 56841950ICE protocol 1촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of ethyl 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]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) δ1.68-1.80 (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, 1 H), 6.87 (d, J=11.2 Hz, 1 H), 6.93 (t, J=7.3 Hz, 1 H), 7.15 (m, 2 H), 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+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.

후처리

  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

출처 및 근거

ORD 기록
ord-de514b66d6364c93af01f2c78d0fe875
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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