3-Methyl-2-butanone → CID 10898559

HRID 431184노트

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HRID 431184 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[N:9]([C@H:12]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([O:19][P:20]([O:23][C@@H:24]([CH2:26][NH:27][C:28]([CH2:30][CH2:31][C@@:32]4([CH3:89])[C:48]5=[N:49][C@@H:34]([C@:35]6([CH3:84])[N-:73][C:38](=[C:39]([CH3:72])[C:40]7[C@:61]([CH2:63][C:64]([NH2:66])=[O:65])([CH3:62])[C@H:60]([CH2:67][CH2:68][C:69]([NH2:71])=[O:70])[C:42](=[CH:43][C:44]8[C:52]([CH3:54])([CH3:53])[C@H:51]([CH2:55][CH2:56][C:57]([NH2:59])=[O:58])[C:46](=[C:47]5[CH3:50])[N:45]=8)[N:41]=7)[C@@H:37]([CH2:74][CH2:75][C:76]([NH2:78])=[O:77])[C@@:36]6([CH2:80][C:81]([NH2:83])=[O:82])[CH3:79])[C@@H:33]4[CH2:85][C:86]([NH2:88])=[O:87])=[O:29])[CH3:25])([O-:22])=[O:21])[C@H:13]3[OH:90])[CH:10]=[N:11][C:4]=2[CH:3]=1.[C-]#N.[Co+3].[I-].C[S+](C)(C)=O.O.O.O.O.O.O.[Co:106](Cl)Cl.[BH4-].[Na+].[OH-].[Na+].CC(C)C(=O)C>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].CO.O.CC(=O)CC>[CH3-:1].[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]2[N:9]([C@H:12]3[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([O:19][P:20]([O:23][CH:24]([CH2:26][NH:27][C:28]([CH2:30][CH2:31][C@@:32]4([CH3:89])[C:48]5=[N:49][C@@H:34]([C@:35]6([CH3:84])[N-:73][C:38](=[C:39]([CH3:72])[C:40]7[C@:61]([CH2:63][C:64]([NH2:66])=[O:65])([CH3:62])[C@H:60]([CH2:67][CH2:68][C:69]([NH2:71])=[O:70])[C:42](=[CH:43][C:44]8[C:52]([CH3:54])([CH3:53])[C@H:51]([CH2:55][CH2:56][C:57]([NH2:59])=[O:58])[C:46](=[C:47]5[CH3:50])[N:45]=8)[N:41]=7)[C@@H:37]([CH2:74][CH2:75][C:76]([NH2:78])=[O:77])[C@@:36]6([CH2:80][C:81]([NH2:83])=[O:82])[CH3:79])[C@@H:33]4[CH2:85][C:86]([NH2:88])=[O:87])=[O:29])[CH3:25])([O-:22])=[O:21])[C@H:13]3[OH:90])[CH:10]=[N:11][C:4]=2[CH:3]=1.[Co+3:106]

참가 물질

11

반응물 6

HCID 112513-Methyl-2-butanoneHCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 517166Dichlorocobalt hexahydrateHCID 4311764Sodium borohydrideHCID 5311498Dtxcid5024346

생성물 1

HCID 10898559CID 10898559수율 509.3%

시약·촉매·용매 4

HCID 62662Ferrous sulfate heptahydrate촉매HCID 887Methanol용매HCID 962Water용매2회HCID 6569Methyl Ethyl Ketone용매

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온도
20 °C

실험 절차

To 390 ml of ion-exchanged water were added 30 g of cyanocobalamin, 14.61 g of trimethylsulfoxonium iodide, 900 mg of iron (II) sulfate heptahydrate, 900 mg of cobalt chloride hexahydrate and 22.5 ml of 2-butanone. After replacing the atmosphere of the system by nitrogen, the mixture was heated in a water bath and a solution of sodium borohydride (12 g)/2N sodium hydroxide (1 ml)/water (60 ml) was added dropwise thereto under stirring at an inner temperature of 20° C. After stirring for 3 hours as it was, the mixture was cooled to 10° C. and then stirred overnight. Thereto was added 24 ml of 3-methyl-2-butanone, followed by stirring for 2 hours. Then, the precipitates were collected by filtration and dried, to give 35 g of a crude product of the title compound. Thereto was added 300 ml of a 50% methanol aqueous solution and the mixture was heated at 35° C, filtered and washed with 120 ml of a 50% methanol aqueous solution. After the mixture was adjusted to pH 7.0 with concentrated hydrochloric acid, 1365 ml of acetone was added dropwise thereto and the mixture was stirred at 10° C. overnight. Precipitated crystals were collected by filtration and dried, to give 25.9 g of the title compound (yield 86.3%).

후처리

  1. temperaturethe mixture was heated in a water bath
  2. stirringAfter stirring for 3 hours as it
  3. temperaturethe mixture was cooled to 10° C.
  4. stirringstirred overnight
  5. stirringby stirring for 2 hours
  6. filtrationThen, the precipitates were collected by filtration
  7. customdried
  8. customto give 35 g of a crude product of the title compound
  9. temperaturethe mixture was heated at 35° C
  10. filtrationfiltered
  11. washwashed with 120 ml of a 50% methanol aqueous solution
  12. additionwas added dropwise
  13. stirringthe mixture was stirred at 10° C. overnight
  14. customPrecipitated crystals
  15. filtrationwere collected by filtration
  16. customdried

출처 및 근거

ORD 기록
ord-78b48bd50bbb4f6f9ee18f65678c2075
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06657057B2

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