Sodium Hydroxide → CID 10898559

HRID 431186Notes

Reaction equation

HRID 431186 reaction equation
[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].[Br-].C[S+](C)(C)=O.O.O.O.O.O.O.[Co:106](Cl)Cl.[BH4-].[Na+].[OH-].[Na+]>CC(=O)CC.O>[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]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 517166Dichlorocobalt hexahydrateHCID 4311764Sodium borohydrideHCID 5311498Dtxcid5024346HCID 11126750Trimethylsulfoxonium Bromide

Product 1

HCID 10898559CID 10898559

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
35 °C

Procedure

To 650 ml of ion-exchanged water were added 50 g of cyanocobalamin, 19.51 g of trimethylsulfoxonium bromide, 3.5 g of cobalt chloride hexahydrate and 37.5 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 (20 g)/2N sodium hydroxide (1 ml)/water (100 ml) was added dropwise thereto under stirring at an inner temperature of 35° C. After stirring for 2 hours as it was, the mixture was cooled to 15° C. and then stirred overnight. Thereto was added 37.5 ml of 2-butanone, followed by stirring for 1 hour. Then, the precipitates were collected by filtration and dried, to give a crude product of the title compound. Thereto was added 700 ml of a 50% methanol aqueous solution, and the mixture was heated at 40° C., filtered and washed with 300 ml of a 50% acetone aqueous solution. After the mixture was adjusted to pH 6.5 with concentrated hydrochloric acid, methanol was evaporated. To the residue was added dropwise 2250 ml of acetone, followed by stirring at 20° C. overnight. Precipitated crystals were collected by filtration and dried, to give 45.0 g of the title compound (yield 90.7%).

Workup

  1. temperaturethe mixture was heated in a water bath
  2. stirringAfter stirring for 2 hours as it
  3. temperaturethe mixture was cooled to 15° C.
  4. stirringstirred overnight
  5. stirringby stirring for 1 hour
  6. filtrationThen, the precipitates were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-e4d6cd3001ef48c2b5a7ecf2eeeb71b9
Source dataset
uspto-grants-2003_12
Patent number
US06657057B2

Reaction notes

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