Sodium Hydroxide → HCID 59392446, compound

HRID 570863Notes

Reaction equation

HRID 570863 reaction equation
C([O:8][C:9]1[C:10](=[O:26])[O:11][C@H:12]([C@H:22]([OH:25])[CH2:23][OH:24])[C:13]=1[O:14]CC1C=CC=CC=1)C1C=CC=CC=1.[OH-].[Na+].[N:29]1[N:30]([C:38]2[CH:43]=[C:42]([CH2:44]Br)[CH:41]=[CH:40][C:39]=2[OH:46])[N:31]=[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=12>C1COCC1.[Pd]>[N:29]1[N:30]([C:38]2[CH:43]=[C:42]([CH:41]=[CH:40][C:39]=2[OH:46])[CH2:44][O:24][CH2:23][C@H:22]([C@H:12]2[O:11][C:10](=[O:26])[C:9]([OH:8])=[C:13]2[OH:14])[OH:25])[N:31]=[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=12

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11162497HCID 11162497, compoundHCID 11739771HCID 11739771, compound

Product 1

HCID 59392446HCID 59392446, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

35 g of (R)-3,4-bisbenzyloxy-5-((R)-1,2-dihydroxyethyl)-5H-furan-2-one (98.2 mmol; 1 eq.) are dissolved in 250 ml of THF under a protective-gas atmosphere, and 3.93 g of sodium hydroxide (98.2 mmol; 1 eq.) are added at 0° C. After 30 min, the 2-benzotriazol-2-yl-4-bromomethylphenol (35.8 g; 117.9 mmol; 1.2 eq.) dissolved in 100 ml of THF is added dropwise, the mixture is stirred at 0° C. for 60 min and at 70° C. for 7 hours. After the reaction solution has been cooled to room temperature, 2 g of Pd/C are added, and the mixture is hydrogenated for 5 hours under a hydrogen atmosphere at 3 bar and 50° C. After filtration through a Celite pad, the solution is neutralised using 2 N HCl solution. The extraction is carried out twice with 250 ml of sat. NaHCO3 solution and 100 ml of sat. NaCl solution. The product is precipitated from the org. phase using 370 ml of heptane.

Workup

  1. additionare added at 0° C
  2. additionis added dropwise
  3. temperatureAfter the reaction solution has been cooled to room temperature
  4. waitthe mixture is hydrogenated for 5 hours under a hydrogen atmosphere at 3 bar and 50° C
  5. filtrationAfter filtration through a Celite pad
  6. extractionThe extraction
  7. customThe product is precipitated from the org

Sources & evidence

ORD record
ord-fc50aed7d4c0402eaa4dc9e60f50d8d0
Source dataset
uspto-grants-2015_05
Patent number
US09023889B2

Reaction notes

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