Hydrochloric Acid → HCID 59551959, compound

HRID 1170066Notes

Reaction equation

HRID 1170066 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:15]=[N:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[N+:25]([O-])=O)[C:12]([OH:28])=[C:11]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.Cl>C(O)C.[Zn]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N:15]2[N:16]=[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]3=[N:25]2)[C:12]([OH:28])=[C:11]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 136034482HCID 136034482, compound

Product 1

HCID 59551959HCID 59551959, compoundYield 51.66%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of XII (3.12 Kg) in ethanol (36 L), a glucose solution (2.496 Kg in 15.6 L 2N NaOH) was added dropwise under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 24 hr. Zinc powder (5.46 Kg) previously activated with HCl solution was charged portionwise to the reaction mixture. The reaction mixture was heated at 60° C. for 4 hr to 6 hr until N-Oxide completely consumed. The reaction mixture was cooled and extracted with 15 liters of a 2:1 hexane:toluene mixture. The organic layer was separated and the aq. layer was re-extracted with a 2:1 hexane:toluene mixture (15 L×3). The organic layer was combined and evaporated up to 90% volume. Upon standing at room temperature the organic layer was solidified. The solid was purified by the slurry wash with 5 L of a 95:5 hexane:toluene mixture followed by a methanol slurry wash (3 L) to give title compound (XIII) (1.34 Kg).

Workup

  1. additionwas charged portionwise to the reaction mixture
  2. customcompletely consumed
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with 15 liters of a 2:1 hexane
  5. customThe organic layer was separated
  6. extractionthe aq. layer was re-extracted with a 2:1 hexane
  7. customevaporated up to 90% volume
  8. customUpon standing at room temperature
  9. customThe solid was purified by the slurry
  10. washwash with 5 L of a 95:5 hexane
  11. washwash (3 L)

Sources & evidence

ORD record
ord-d22f6135d7a442b6842777d0aa75701d
Source dataset
uspto-grants-2010_11
Patent number
US07825257B1

Reaction notes

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