Sodium Azide → HCID 86588996, compound

HRID 352992Notes

Reaction equation

HRID 352992 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([C@H:15]2[O:19][C:18](=[O:20])[C:17]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:16]2[O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[OH:14])(=O)=O)=CC=1.[N-:37]=[N+:38]=[N-:39].[Na+]>CO>[N:37]([CH2:12][C@@H:13]([C@H:15]1[O:19][C:18](=[O:20])[C:17]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:16]1[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[OH:14])=[N+:38]=[N-:39]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 18345880HCID 18345880, compound

Product 1

HCID 86588996HCID 86588996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-5-[2-(4-methylphenylsulfonyloxy)-(S)-1-hydroxyethyl]-3,4dibenzyloxy-5H-furan-2-one (5)† (550 mg, 1.1 mmol), sodium azide (190 mg, 1.7 mmol) and methanol (2 ml) were heated under reflux for 6 hours. The reaction mixture was cooled and most of the solvent removed by evaporation at room temperature. The resulting material was partitioned between water (25 ml) and dichloromethane (25 ml) and the aqueous phase extracted with dichloromethane (25 ml). The combined organic fractions were dried (MgSO4), filtered and volatile components evaporated under reduced pressure (8 mm/Hg) at room temperature to give the product (6) as a yellow waxy solid (375 mg, 89%). This material was used without further purification.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureThe reaction mixture was cooled and most of the solvent
  3. customremoved by evaporation at room temperature
  4. customThe resulting material was partitioned between water (25 ml) and dichloromethane (25 ml)
  5. extractionthe aqueous phase extracted with dichloromethane (25 ml)
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. filtrationfiltered
  8. customvolatile components evaporated under reduced pressure (8 mm/Hg) at room temperature

Sources & evidence

ORD record
ord-f8b562086a224db1a1f2680d132788e4
Source dataset
uspto-grants-2004_06
Patent number
US06749832B2

Reaction notes

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