Hydrochloric Acid → 2-[(2S,3R,5S,6S)-6-[(2R,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5S)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-3,5-dimethyloxan-2-yl]ethaneperoxoic acid

HRID 329777Notes

Reaction equation

HRID 329777 reaction equation
[Na].[CH3:2][CH2:3][C@@H:4]([C:25]([C@H:27]([C@@H:29]([OH:45])[C@H:30]([C@H:32]1[O:37][C@@H:36]([CH2:38][C:39]([O:41][OH:42])=[O:40])[C@H:35]([CH3:43])[CH2:34][C@@H:33]1[CH3:44])[CH3:31])[CH3:28])=[O:26])[C@H:5]1[O:9][C@@:8]([C@:11]2([OH:23])[O:15][C@@:14]([C@@H:18]([OH:21])[CH2:19][CH3:20])([CH2:16][CH3:17])[CH2:13][C@H:12]2[CH3:22])([CH3:10])[CH2:7][C@@H:6]1[CH3:24].Cl>O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(O)C>[CH3:2][CH2:3][C@@H:4]([C:25]([C@H:27]([C@@H:29]([OH:45])[C@H:30]([C@H:32]1[O:37][C@@H:36]([CH2:38][C:39]([O:41][OH:42])=[O:40])[C@H:35]([CH3:43])[CH2:34][C@@H:33]1[CH3:44])[CH3:31])[CH3:28])=[O:26])[C@H:5]1[O:9][C@@:8]([C@:11]2([OH:23])[O:15][C@@:14]([C@@H:18]([OH:21])[CH2:19][CH3:20])([CH2:16][CH3:17])[CH2:13][C@H:12]2[CH3:22])([CH3:10])[CH2:7][C@@H:6]1[CH3:24]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86741790Sodium lysocellin2×

Product 1

HCID 445670512-[(2S,3R,5S,6S)-6-[(2R,3S,4S,6R)-6-[(2S,3S,5S)-5-[(2R,3R,5S)-5-ethyl-2-hydroxy-5-[(1S)-1-hydroxypropyl]-3-methyloxolan-2-yl]-3,5-dimethyloxolan-2-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-3,5-dimethyloxan-2-yl]ethaneperoxoic acid

Reagents, catalysts & solvents 2

HCID 20271390ZINC;diacetate;hydrateCatalyst2×HCID 702EthanolSolvent2×

Procedure

3.9 g sodium lysocellin @ (0.006 moles) and 1.4 g zinc acetate hydrate [Zn(Ac)2 0.2H2O]@ (0.006 mole) were mixed together in 30 ml denatured ethanol (3A). The sodium lysocellin was first suspended in the ethanol and stirred, and the zinc acetate hydrate was added, and the suspension stirred at room temperature until everything was dissolved. The pH was then adjusted to a range of 2-4 with 37% HCl. Stirring was continued for 20-30 minutes until precipitation of a birefringent material started. Precipitation was continued by adding water dropwise (holding pH at 4) until about 60 ml of water was added. The resulting crystalline precipitate of the free acid of lysocellin was isolated and dried. Th resulting free acid of lysocellin comprises birefringent crystals.

Workup

  1. stirringthe suspension stirred at room temperature until everything
  2. dissolutionwas dissolved
  3. stirringStirring
  4. customwas continued for 20-30 minutes until precipitation of a birefringent material
  5. customPrecipitation
  6. additionby adding water dropwise (holding pH at 4) until about 60 ml of water
  7. additionwas added

Sources & evidence

ORD record
ord-8fd661e850be4b5592af916d143790a0
Source dataset
uspto-grants-1990_01
Patent number
US04892960

Reaction notes

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