Dichloroisoproterenol → HCID 18672513, 화합물

HRID 1057984노트

반응식

HRID 1057984 반응식
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:27]=[CH:26][C:17]([CH2:18][NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.[CH:35]([NH:38][CH2:39][CH:40]([C:42]1[CH:47]=[CH:46]C(Cl)=[C:44]([Cl:49])[CH:43]=1)[OH:41])(C)C.[CH2:50]([Cl:52])Cl>CCOC(C)=O>[Cl:49][C:44]1[CH:43]=[C:42]([CH:40]([OH:41])[CH2:39][N:38]([CH3:35])[C:2](=[O:4])[NH:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:18][NH:19][C:20](=[O:25])[C:21]([CH3:23])([CH3:24])[CH3:22])=[CH:26][CH:27]=2)[CH:47]=[CH:46][C:50]=1[Cl:52]

참가 물질

7

반응물 5

HCID 5806DichloroisoproterenolHCID 6344Dichloromethane3회HCID 8471Triethylamine2회HCID 94429TriphosgeneHCID 18672514HCID 18672514, 화합물

생성물 1

HCID 18672513HCID 18672513, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a 0° C. solution of 0.048 g (0.16 mmol) triphosgene in 1 mL CH2Cl2 was slowly added a solution of 0.1 g 0.48 mmol) N-(4-amino-benzyl)-2,2-dimethyl-propionamide and 0.07 mL (0.5 mmol) triethylamine in 8 mL CH2Cl2 over 20 min. The reaction mixture was allowed to warm to room temperature for 15 min., then recooled to 0° C. whereupon a solution of 0.2 g (0.9 mmol) 2-methylamino-1-(3,4-dichlorophenyl)ethanol (prepared as in scheme 1, step 2) and 0.1 mL (0.5 mmol) triethylamine in 2 mL CH2Cl2 was added. The reaction mixture was allowed to warn to room temperature and stir 1 hour, then diluted with 100 mL EtOAc, washed with 100 mL each of, saturated aqueous NaHCO3, 10% aqueous KHSO4, and brine, then dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (2.5×12 cm silica gel, linear gradient 3-5% MeOH/CH2Cl2) afforded 0.14 g N-(4-{3-[2-(3,4-Dichloro-phenyl)-2-hydroxy-ethyl]-3-methyl-ureido}-benzyl)-2,2-dimethyl-propionamide. 1H NMR(300 mHz, CD3OD) δ 7.61 (d, 1H, J=1.83 Hz); 7.49 (d, 1H, J=8.24 Hz); 7.35 (dd, 1H, J=1.83 and 8.24 Hz); 7.26 (d, 2H, J=8.54 Hz); 7.17 (d, 2H, J=8.55 Hz); 4.93 (m, 1H); 4,31 (s, 2H); 3.54 (m, 2H); 2.96 (s, 3H); 1.20 (s, 9H).

후처리

  1. additionwas added
  2. customto warn to room temperature
  3. washwashed with 100 mL each of, saturated aqueous NaHCO3, 10% aqueous KHSO4, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (2.5×12 cm silica gel, linear gradient 3-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-6b78089dbe2c4e539dff1df615d0e2d4
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515023B2

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