Nitrogen → HCID 54537147、化合物

HRID 865455ノート

反応式

HRID 865455 の反応式
CCN(CC)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.S[CH2:51][CH:52](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:52]([CH3:51])[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]

参加物

11

反応物 8

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

生成物 1

HCID 54537147HCID 54537147、化合物

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-18d0c96fb0a44dfd8f0d713564a6e57c
出典データセット
uspto-grants-1996_10
特許番号
US05565473

反応ノート

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