HCID 54539058, compound → HCID 131712512, compound

HRID 848578Notes

Reaction equation

HRID 848578 reaction equation
[CH2:1]([OH:24])[C@@H:2]([OH:23])[C@H:3]([OH:22])[C@H:4]([O:9][C@@H:10]1[O:15][C@H:14]([C:16]([OH:18])=[O:17])[C@@H:13]([OH:19])[C@H:12]([OH:20])[C@H:11]1[OH:21])[C@@H:5]([NH2:8])[CH:6]=[O:7].BrCC([C@H:29]1[CH2:46][CH2:45][C@@:44]2([CH3:47])[C:31](=[CH:32][CH2:33][C@@H:34]3[C@@H:43]2[CH2:42][CH2:41][C@@:39]2([CH3:40])[C@H:35]3[CH2:36][CH2:37][C:38]2=[O:48])[CH2:30]1)=O>CS(C)=O.[Ag]>[CH2:1]([OH:24])[C@@H:2]([OH:23])[C@H:3]([OH:22])[C@H:4]([O:9][C@@H:10]1[O:15][C@H:14]([C:16]([OH:18])=[O:17])[C@@H:13]([OH:19])[C@H:12]([OH:20])[C@H:11]1[OH:21])[C@@H:5]([NH2:8])[CH:6]=[O:7].[CH3:40][C@@:39]12[C:38](=[O:48])[CH2:37][CH2:36][C@H:35]1[C@@H:34]1[CH2:33][CH:32]=[C:31]3[CH2:30][C@@H:29]([OH:7])[CH2:46][CH2:45][C@:44]3([CH3:47])[C@H:43]1[CH2:42][CH2:41]2

Participants

5

Reactant 2

HCID 54539058HCID 54539058, compoundHCID 71586761Chondrosine

Product 1

HCID 131712512HCID 131712512, compound

Reagents, catalysts & solvents 2

HCID 23954SilverCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

1.133 Grams (0.00245 mole) of silver salt of chondrosine was dissolved in 70 ml of DMSO (dimethylsulfoxide) and 0.84 g of the compound (1) was added to the solution to react them at room temperature for 2 days. After the reaction, AgBr was separated by a centrifugal separation and DMSO was distilled off from the resulting supernatant at 45° to 50° C. under a reduced pressure and then, 70 ml of ethanol was added to the residual solid and a floating insoluble material was separated and a filtrate was concentrated under a reduced pressure and poured into 2 ml of cold water to precipitate the product. The precipitate was dried and washed with ether and dried to obtain 0.36 g of a conjugate of chondrosine-dehydroepiandrosterone having the formula ##STR1##

Workup

  1. customto react them at room temperature for 2 days
  2. customwas separated by a centrifugal separation and DMSO
  3. distillationwas distilled off from the resulting supernatant at 45° to 50° C. under a reduced pressure
  4. addition70 ml of ethanol was added to the residual solid
  5. customa floating insoluble material was separated
  6. concentrationa filtrate was concentrated under a reduced pressure
  7. additionpoured into 2 ml of cold water
  8. customto precipitate the product
  9. customThe precipitate was dried
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-b5b1ab4784fa4907a795a38cb025b728
Source dataset
uspto-grants-1981_10
Patent number
US04296233

Reaction notes

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