Ammonia → HCID 53660528, compound

HRID 2397473Notes

Reaction equation

HRID 2397473 reaction equation
[NH:1]([C:3]([C@@H:5]([C@@H:14]([C@@H:23]([CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)O)[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4])[NH2:2].[CH2:34](OC(OCC)OCC)C.C([C:46]1[CH:50]=[C:49](CC)[N:48]([CH:53]2O[C@H](COCC3C=CC=CC=3)[C@@H](OCC3C=CC=CC=3)[C@H]2OCC2C=CC=CC=2)[N:47]=1)C.[NH3:83]>CO.C(O)C>[NH2:83][C:49]1[N:48]=[CH:53][N:47]=[C:46]2[N:1]([C@@H:3]3[O:4][C@H:23]([CH2:25][O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C@@H:14]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C@H:5]3[O:6][CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:2]=[CH:34][C:50]=12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 31214Ethyl orthoformateHCID 53641074HCID 53641074, compoundHCID 54139660HCID 54139660, compound

Product 1

HCID 53660528HCID 53660528, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

1.9 g (4.4 mmoles) of 1-hydrazino-2,3,5-tri-O-benzyl-D-ribose are dissolved in 10 ml of absolute methanol. To the solution 0.54 g (4.4 mmoles) of ethoxymethylenemalonodinitrile, dissolved in 10 ml of absolute methanol, are added dropwise. Slight heating occurs. Stirring is carried out at room temperature for 24 hours and following this for completion of the reaction refluxing is carried out for 30 minutes. Following this the product is separated by column chromatography. As an eluting agent use is made of a mixture of benzene and acetone (85:15). Rf = 0.61. A yellow oil is obtained which is boiled with 7 ml of orthoformic acid triethylester for 3 hours under reflux. (Bath temperature 160° C.)(3). After removal of the remaining ortho-ester the oil obtained is dissolved in 13 ml of ethanol. NH3 is introduced into the solution at room temperature (for four hours). After removal of the ethanol purification is carried out by column chromatography (benzene to acetone = 50 to 50). Rf = 0.58. A yellow oil is obtained. Yield: 1.36 g (52 %).

Workup

  1. additionare added dropwise
  2. temperatureSlight heating
  3. temperaturerefluxing
  4. waitis carried out for 30 minutes
  5. customis separated by column chromatography
  6. additionAs an eluting agent use is made of a mixture of benzene and acetone (85:15)
  7. customA yellow oil is obtained which
  8. temperatureunder reflux
  9. customAfter removal of the remaining ortho-ester the oil
  10. customobtained
  11. customAfter removal of the ethanol purification
  12. customA yellow oil is obtained

Sources & evidence

ORD record
ord-a79800ee666a4a508514f68c64bb7c6c
Source dataset
uspto-grants-1977_05
Patent number
US04021542

Reaction notes

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