Dimethylformamide → HCID 86735818, compound

HRID 839955Notes

Reaction equation

HRID 839955 reaction equation
[CH2:1]([C@@:8]1([OH:32])[C@H:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:11]([CH2:21][OH:22])[O:10][C@H:9]1[N:23]1[CH:30]=[C:29]([Br:31])[C:27](=[O:28])[NH:26][C:24]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:33][CH:34]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:35](O)=[O:36].CN(C)C=O.C1(N=C=NC2CCCCC2)CCCCC1>C1CCCCC1>[SH:33][CH:34]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:35]([O:22][CH2:21][C@H:11]1[O:10][C@@H:9]([N:23]2[CH:30]=[C:29]([Br:31])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([OH:32])[C@@H:12]1[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 187622982-Mercaptooctadecanoic acidHCID 70614117HCID 70614117, compound

Product 1

HCID 86735818HCID 86735818, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
80 °C

Procedure

10 mmol of 2',3'-O-dibenzyl-5-bromouridine and 20 mmol of 2-mercaptostearic acid were added to 400 ml of dimethylformamide containing 40 ml of N,N'-dicyclohexylcarbodiimide, and the mixture was stirred for 3 hours. The resulting reaction mixture was then concentrted at 0.2 atm. at a temperature of 60° C. 200 ml of cyclohexane was added to the residue, and the mixture was heated at a temperature of 80° C for 2 hours while refluxing. The reaction mixture was filtered to recover the residue, and the residue was washed three times with cyclohexane. The resulting residue was then added to 100 ml of dimethylformamide followed by heating at a temperature of 80° C to dissolve the residue. The solution was allowed to cool to room temperature and 100 ml of water was added to the solution. The white precipitate formed was collected by filtration and air-dried to obtain 5.6 mmol (56% yield) of 5'-O-(2-mercaptostearoyl)-2',3' -O-dibenzyl-5-bromouridine as a white powder.

Workup

  1. customThe resulting reaction mixture
  2. customwas then concentrted at 0.2 atm. at a temperature of 60° C
  3. temperaturewhile refluxing
  4. filtrationThe reaction mixture was filtered
  5. customto recover the residue
  6. washthe residue was washed three times with cyclohexane
  7. additionThe resulting residue was then added to 100 ml of dimethylformamide
  8. temperatureby heating at a temperature of 80° C
  9. dissolutionto dissolve the residue
  10. temperatureto cool to room temperature
  11. addition100 ml of water was added to the solution
  12. customThe white precipitate formed
  13. filtrationwas collected by filtration
  14. customair-dried

Sources & evidence

ORD record
ord-07c7e2b040c549a9857ae5b93eb5db6f
Source dataset
uspto-grants-1978_06
Patent number
US04097665

Reaction notes

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