Chlorosuccinimide → HCID 66727923, 화합물

HRID 1961549노트

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HRID 1961549 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[N:19][OH:20])=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(Cl)C(=O)C1.C(=O)([O-])O.[K+].[Cl:34][C:35]1[CH:40]=[C:39]([C:41]([C:43]([F:46])([F:45])[F:44])=[CH2:42])[CH:38]=[C:37]([Cl:47])[CH:36]=1>CN(C=O)C.ClCCl.CCCCCC.C(OCC)(=O)C.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH2:42][C:41]([C:39]4[CH:38]=[C:37]([Cl:47])[CH:36]=[C:35]([Cl:34])[CH:40]=4)([C:43]([F:44])([F:46])[F:45])[O:20][N:19]=3)=[CH:16][CH:17]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

10

반응물 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 766614793-[4-(Hydroxyimino-methyl)-phenyl]-azetidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 66727923HCID 66727923, 화합물

시약·촉매·용매 5

HCID 887Methanol용매HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

To a stirred solution of 3-[4-(Hydroxyimino-methyl)-phenyl]-azetidine-1-carboxylic acid tert-butyl ester (Preparation 39, 1 g, 3.62 mmol, 1.0 equivalents) in DMF (6.0 mL) was added NCS (725.26 mg, 5.43 mmol, 1.5 equivalents) and heated to 50° C. for 1 hour. Progress of the reaction was monitored by TLC using 5% methanol in dichloromethane. After complete consumption of starting material, reaction was cooled to 0° C. followed by the addition of potassium hydrogen carbonate (543.18 mg, 5.43 mmol, 1.5 equivalents) and pre-dissolved solution of 1,3-Dichloro-5-(1-trifluoromethyl-vinyl)-benzene (1.04 g, 4.345 mmol, 1.2 equivalents) in DMF (4.0 mL). Resulting reaction was stirred at room temperature for 16 hours under nitrogen atmosphere. Progress of the reaction was monitored by TLC using 20% ethyl acetate in hexane and visualized in UV light (254 nm). Reference of required product was 0.6 and 0.5 for starting material. After consumption of starting material, reaction mixture was quenched with water (40 mL) extracted with diethyl ether (3×50 mL). Combined organic layer was washed with brine (20 mL) and dried over anhydrous sodium sulphate and concentrated in vacuo to afford (1.50 g, crude). Further purification by column chromatography (on neutral alumina) using 10% ethyl acetate in hexane as eluent afforded off white solid 1.3 g (69.84%). 1H NMR and LC-MS were consistent. 1H NMR (400 MHz, DMSO-d6) δ 1.39 (s, 9H), 3.84 (m, 3H), 4.25-4.38 (m, 4H), 7.47 (d, J=8 Hz, 2H), 7.62 (d, J=1 Hz, 2H), 7.71 (d, J=8 Hz, 2H), 7.81 (t, J=2 Hz, 1H). LC-MS (m/z):=513 (M−H).

후처리

  1. customAfter complete consumption of starting material, reaction
  2. temperaturewas cooled to 0° C.
  3. customResulting
  4. customreaction

출처 및 근거

ORD 기록
ord-72f42ce857784ca5808e5eb910756e2b
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415310B2

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