HCID 86604589, compound → HCID 86760347, compound

HRID 1371831Notes

Reaction equation

HRID 1371831 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:21]=[CH:20][O:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[N+]=[N-].C(Cl)[Cl:23].CO.C1COCC1.O>>[Cl-:23].[O:19]1[CH:20]=[CH:21][C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:7]3[CH2:6][C@H:5]([CH2:4][NH3+:1])[O:9][C:8]3=[O:10])=[CH:12][CH:13]=2)=[N:18]1

Participants

3

Reactant 2

HCID 86604589HCID 86604589, compoundHCID 86760348HCID 86760348, compound

Product 1

HCID 86760347HCID 86760347, compound

Procedure

[(5R)-3-(4-Isoxazol-3-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate (Intermediate 7,400 mg, 1.18 mmol), sodium azide (99 mg, 1.53 mmol), 18 crown-6 (23.6 mg, 0.089 mmol) and tetrabutylammonium iodide (28.2 mg, 0.076 mmol) were combined in DMF (5 ml) and heated to 60° C. for 4 hours. EtOAc (20 ml) was added and the organic layers were washed with brine (3×20 ml), dried over Na2SO4 and concentrated under vacuum to yield (5R)-5-(azidomethyl)-3-(4-isoxazol-3-ylphenyl)-1,3-oxazolidin-2-one. (5R)-5-(Azidomethyl)-3-(4-isoxazol-3-ylphenyl)-1,3-oxazolidin-2-one (300 mg, 1.045 mmol) was added to CH2Cl2:MeOH:THF:H2O 10:10:10:2 and then polystyrene triphenylphosphine resin (2650 mg, 4.18 mmol) was added. The reaction was allowed to stir overnight and then the resin was filtered and washed multiple times with dichloromethane and methanol. The filtrate was concentrated in vacuo and then dissolved in dichloromethane (10 ml) followed by addition of 2N HCl in ether (0.5 ml). The precipitate was collected and washed with ether (2×20 ml) and then dried under vacuum to yield the title product (300 mg).

Workup

  1. filtrationthe resin was filtered
  2. washwashed multiple times with dichloromethane and methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutiondissolved in dichloromethane (10 ml)
  5. additionfollowed by addition of 2N HCl in ether (0.5 ml)
  6. customThe precipitate was collected
  7. washwashed with ether (2×20 ml)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-48b3bdf864a84722b59b07565fa0bd38
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

Loading…