Hydrochloric Acid → CID 10898559

HRID 431181Notes

Reaction equation

HRID 431181 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+3:93].[I-].C[S+](C)C.[BH4-].[Na+].[OH-].[Na+].Cl>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2].CC(C)=O.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+3:93]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 75127Trimethylsulfonium iodideHCID 4311764Sodium borohydrideHCID 5311498Dtxcid5024346

Product 1

HCID 10898559CID 10898559Yield 171.4%

Reagents, catalysts & solvents 4

HCID 62662Ferrous sulfate heptahydrateCatalystHCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
40 °C

Procedure

To 260 ml of ion-exchanged water were added 20 g of cyanocobalamin, 6.02 g of trimethylsulfonium iodide and 800 mg of iron(II) sulfate heptahydrate. The mixture was heated in a water bath and, after replacing the atmosphere of the system by nitrogen, a solution of sodium borohydride (8 g)/2N sodium hydroxide (0.2 ml)/water (40 ml) and 15 ml of 2-butanone were added dropwise thereto under stirring at an inner temperature of 40° C. over 20 minutes, respectively. After stirring for 15 minutes as it was, the mixture was cooled to 15° C. Further, 15 ml of 2-butanone was added thereto, followed by stirring overnight. The precipitates were collected by filtration and dried, to give 21.4 g of a crude product of the title compound. Thereto was added 200 ml of a 50% acetone aqueous solution, and the mixture was heated, adjusted to pH 6.5 with concentrated hydrochloric acid and then filtered. After washing with 40 ml of a 50% acetone aqueous solution, 630 ml of acetone was added dropwise to the filtrate, followed by stirring at 15° C. overnight. Precipitated crystals were collected by filtration and dried, to give 17 g of the title compound (yield 86%).

Workup

  1. temperatureThe mixture was heated in a water bath
  2. stirringAfter stirring for 15 minutes as it
  3. temperaturethe mixture was cooled to 15° C
  4. stirringby stirring overnight
  5. filtrationThe precipitates were collected by filtration
  6. customdried
  7. customto give 21.4 g of a crude product of the title compound
  8. temperaturethe mixture was heated
  9. filtrationfiltered
  10. washAfter washing with 40 ml of a 50% acetone aqueous solution, 630 ml of acetone
  11. additionwas added dropwise to the filtrate
  12. stirringby stirring at 15° C. overnight
  13. customPrecipitated crystals
  14. filtrationwere collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-1e0e0f24d4c341f8b3f1b67aac209003
Source dataset
uspto-grants-2003_12
Patent number
US06657057B2

Reaction notes

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