Triethylamine → methyl (S)-3-chloro-4-[2-[4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate

HRID 354491노트

반응식

HRID 354491 반응식
[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.[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([NH2:48])[CH3:47])[C:37]([O:39][CH3:40])=[O:38].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]=[CH:42][C:43]=1[O:44][CH2:45][C@@H:46]([NH:48][C:18](=[O:20])[CH2:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[O:32])=[CH:16][CH:15]=1)[CH3:47])[C:37]([O:39][CH3:40])=[O:38]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 23512272pentafluorophenyl 4-[N'-(2-methylphenyl)ureido]phenylacetateHCID 86587793methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate

생성물 1

HCID 86587792methyl (S)-3-chloro-4-[2-[4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate수율 42%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of pentafluorophenyl 4-[N′-(2-methylphenyl)ureido]phenylacetate (508 mg, 1.13 mmol), methyl (S)-3-chloro-4-(2-amino-1-propoxy)benzoate (275 mg, 1.13 mmol) and Et3N (0.240 mL, 1.72 mmol) in DMF (10 mL) was stirred at room temp overnight. The mixture was diluted with EtOAc, and the solution was washed with 0.5 N HCl, sat. NaHCO3, brine, dried over Na2SO4, and evaporated. The residue was recrystallized from MeOH—CHCl3-n-hexane to give 240 mg (42%) methyl (S)-3-chloro-4-[2-[4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate as a white crystalline powder. 1H-NMR (DMSO-d6) δ1.21 (d, 3H, J=6.4 Hz), 2.25 (s, 3 H), 3.33 (s, 2 H), 3.82 (s, 3 H), 4.04-4.14 (m, 3H), 6.90-6.94 (m, 1H), 7.11-7.16 (m, 4H), 7.29-7.38 (m, 3H), 7.83-7.94 (m, 3H), 8.13-8.17 (m, 2H), 9.34 (s, 1 H); MS(FAB) m/z 510 (M30).

후처리

  1. washthe solution was washed with 0.5 N HCl, sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was recrystallized from MeOH—CHCl3-n-hexane

출처 및 근거

ORD 기록
ord-b6d759512e9747b5aac11493f0a3174f
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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