Ammonium Chloride → HCID 86636537, compound

HRID 1641372Notes

Reaction equation

HRID 1641372 reaction equation
[C:1]([O:5][C:6]([CH2:8][C@:9](C(=O)C1C=CC=CC=1)([C@:11](C(=O)C1C=CC=CC=1)([CH2:13][OH:14])[OH:12])[OH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.C[O-].[Na+].[Cl-].[NH4+]>CO>[C:1]([O:5][C:6]([CH2:8][C@H:9]([C@H:11]([CH2:13][OH:14])[OH:12])[OH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23694274Sodium methanolate methanolHCID 66738979HCID 66738979, compound

Product 1

HCID 86636537HCID 86636537, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.61 kg (1.53 mol) of 1-t-butoxy-2-deoxy-3,4-dibenzoyl-L-ribose was dissolved in 6.02 liters of methanol for 30 minutes, and 0.041 kg of 25 w % sodium methoxide methanol solution was added thereto. The mixture solution was stirred at room temperature at room temperature. After completion of the reaction, 0.013 kg of ammonium chloride was added to the reaction solution, which was then stirred for 2 hours, and 0.038 kg of celite was added thereto. Next, the solution was stirred for 30 minutes, and then concentrated. To the concentrated residue, 2.531 liters of ethyl acetate was added at 35-45° C., and the solution was stirred at the same temperature for 2-3 hours. The stirred solution was filtered using 0.038 kg of celite, and was washed with 0.422 liters of ethyl acetate, and then completely concentrated, thus obtaining 0.29 kg (100% yield) of 1-t-butoxy-2-deoxy-L-ribose.

Workup

  1. additionwas added to the reaction solution, which
  2. stirringwas then stirred for 2 hours
  3. addition0.038 kg of celite was added
  4. stirringNext, the solution was stirred for 30 minutes
  5. concentrationconcentrated
  6. additionTo the concentrated residue, 2.531 liters of ethyl acetate was added at 35-45° C.
  7. stirringthe solution was stirred at the same temperature for 2-3 hours
  8. filtrationThe stirred solution was filtered
  9. washwas washed with 0.422 liters of ethyl acetate
  10. concentrationcompletely concentrated

Sources & evidence

ORD record
ord-c15b8bbda1584119bda728e9107d7397
Source dataset
uspto-grants-2012_02
Patent number
US08114987B2

Reaction notes

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