Nitrogen → HCID 54537147, 화합물

HRID 326909노트

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HRID 326909 반응식
CCN([CH2:6][CH3:7])CC.[CH3:8][S:9](Cl)(=O)=O.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:27]=1)O)(=[O:15])[CH3:14].C([O-])(O)=O.[Na+].S([O-])(=O)(=O)C.SCC(C)[C:53]([O:55][CH2:56][CH3:57])=[O:54].C([O-])([O-])=O.[Cs+].[Cs+].N#N>C(Cl)Cl.CC#N>[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH:24]([S:9][CH2:8][CH:6]([CH3:7])[C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:27]=1)(=[O:15])[CH3:14]

참가 물질

11

반응물 8

HCID 947NitrogenHCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 15289599Ethyl 3-mercapto-2-methylpropanoateHCID 53725555HCID 53725555, 화합물

생성물 1

HCID 54537147HCID 54537147, 화합물

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
-10 °C

실험 절차

At -40° C., Et3N (triethylamine) (1.60 mL, 11.5 mmol) and methanesulfonyl chloride (750 μl, 9.69 mmol) were added to a solution of the alcohol of Step 6 (7.39 mmol) in 74 mL of CH2Cl2 and the mixture was stirred at -40° C. for an hour and at -10° C. for 45 minutes. Saturated aq NaHCO3 was then added and the mesylate was extracted with CH2Cl2, dried over Na2SO4 and concentrated. To this mesylate in 150 mL of anhydrous CH3CN, ethyl 3-mercapto-2-methylpropanoate (Example 4, Step 6; 2.20 mL, approx. 15 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were added and the mixture was stirred under a stream of N2 for 2 hours. 25% Aq NH4OAc was then added and the title product was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene.

후처리

  1. extractionthe mesylate was extracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. extractionthe title product was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography on silica with EtOAc

출처 및 근거

ORD 기록
ord-2c41e1f9d5c04b79aedec6785c467dcc
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270324

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