Potassium Hydroxide → (2R,3S,4R,5R,6S)-2-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-5-chloro-6-(hydroxymethyl)oxane-3,4-diol

HRID 1363430

Reaction equation

HRID 1363430 reaction equation
CC([O:4][CH2:5][C@H:6]1[O:11][C@H:10]([O:12][C@:13]2([CH2:22][Cl:23])[O:17][C@H:16]([CH2:18][Cl:19])[C@@H:15]([OH:20])[C@@H:14]2[OH:21])[C@H:9]([OH:24])[C@@H:8]([OH:25])[C@H:7]1[Cl:26])=O.[OH-].[K+]>CO>[CH2:5]([OH:4])[C@@H:6]1[O:11][C@H:10]([O:12][C@:13]2([CH2:22][Cl:23])[O:17][C@H:16]([CH2:18][Cl:19])[C@@H:15]([OH:20])[C@@H:14]2[OH:21])[C@@H:9]([OH:24])[C@@H:8]([OH:25])[C@H:7]1[Cl:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10094747Sucralose 6-acetate

Product 1

HCID 70683051(2R,3S,4R,5R,6S)-2-[(2R,3S,4S,5S)-2,5-bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy-5-chloro-6-(hydroxymethyl)oxane-3,4-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g Sucralose-6-acetate was dissolved in 150 ml methanol, and the pH value of the solution was adjusted into 11 with KOH. The reaction was kept at 45° C. for 4 hours, then decolored with activated carbon, filtered and the filtrate was concentrated. 6 ml Water was added to the concentrate in 70° C. The resulting solution was Cooled gradually to room temperature and kept standing, then Filtered to obtain the product sucralose, 12.3 g. It was verified that the purity was over 99%.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. addition6 ml Water was added to the
  4. concentrationconcentrate in 70° C
  5. filtrationFiltered

Sources & evidence

ORD record
ord-e2d2a409c42b49a4a800d75ed41aa537
Source dataset
uspto-grants-2011_02
Patent number
US07884203B2

Linked notes

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