Hydrazine → HCID 15060541, compound

HRID 2397479Notes

Reaction equation

HRID 2397479 reaction equation
[NH2:1][NH2:2].[CH2:3]([O:10][C@@H:11]([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)[OH:24])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:12]=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.O1CCCC1>[NH:1]([C:12]([C@H:11]([C@@H:14]([C@@H:23]([CH2:25][O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[OH:24])[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:13])[NH2:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 11316111HCID 11316111, compound

Product 1

HCID 15060541HCID 15060541, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.8 g (119 mmoles) of anhydrous hydrazine in 10 ml of absolute methanol a solution of 5 g (11.9 mmoles) of 2,3,5-tri-O-benzyl-D-arabinose in 10 ml of absolute tetrahydrofuran (THF) is added dropwise while stirring and cooling in an ice bath at a moderate speed. After 10 minutes the ice bath is removed and the solution is stirred for 6 hours at room temperature. Then the solvent is removed with the superfluous hydrazine, and the remaining yellowish oil is dried for removal of the last traces of hydrazine for one day under a continuous oil pump vacuum.

Workup

  1. temperaturecooling in an ice bath at a moderate speed
  2. customAfter 10 minutes the ice bath is removed
  3. stirringthe solution is stirred for 6 hours at room temperature
  4. customThen the solvent is removed with the superfluous hydrazine
  5. dry with materialthe remaining yellowish oil is dried for removal of the last traces of hydrazine for one day under a continuous oil pump vacuum

Sources & evidence

ORD record
ord-34b852aaf429419ca5f2d7b0e861f399
Source dataset
uspto-grants-1977_05
Patent number
US04021542

Reaction notes

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