Hydrochloric Acid → HCID 131726300, compound

HRID 459037Notes

Reaction equation

HRID 459037 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:36][C@H:35]([CH2:37][N:38]5[CH:42]=[CH:41][N:40]=[N:39]5)[O:34][C:33]4=[O:43])=[CH:28][C:27]=3[F:44])=[CH:22][N:21]=2)[CH2:16]1)([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].CO.C(Cl)Cl.Cl.CCOCC>O1CCOCC1>[NH4+:18].[NH4+:18].[P:1]([O-:8])([O-:3])([O:13][CH2:14][C@H:15]1[O:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([N:32]4[CH2:36][C@H:35]([CH2:37][N:38]5[CH:42]=[CH:41][N:40]=[N:39]5)[O:34][C:33]4=[O:43])=[CH:28][C:27]=3[F:44])=[CH:22][N:21]=2)[CH2:16]1)=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 21226129Dichloromethane methanolHCID 58758431HCID 58758431, compound2×

Product 1

HCID 131726300HCID 131726300, compoundYield 296.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Di-tert-butyl [(5S)-3-(5-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl phosphate (Intermediate 19, 6.07 g, 9.63 mmol) was added to MeOH:CH2Cl2 1:1 (100 ml). 4 N HCl in dioxane (15 ml) was then added and the reaction was allowed to stir at room temperature for 2 hours. The solution was then poured into Et2O (800 ml) and the precipitate was collected by vacuum filtration. The precipitate was then washed with Et2O (3×100 ml) and then dried in vacuo for 1 hour. The resulting solid was then dissolved in a mixture of distilled water (60 ml) and concentrated ammonium hydroxide (5 ml). The aqueous solution was then frozen in a round bottom flask using dry ice/acetone and placed on a freeze dryer for 2 days. The solid was then suspended in a mixture of MeOH (60 ml) and Et2O (200 ml) and then filtered. The solid was washed with additional Et2O (2×100 ml) and then placed in a round bottom flask in vacuo overnight to yield the product (5.262 g).

Workup

  1. filtrationthe precipitate was collected by vacuum filtration
  2. washThe precipitate was then washed with Et2O (3×100 ml)
  3. customdried in vacuo for 1 hour
  4. dissolutionThe resulting solid was then dissolved in a mixture of distilled water (60 ml) and concentrated ammonium hydroxide (5 ml)
  5. temperatureThe aqueous solution was then frozen in a round bottom flask
  6. waitplaced on a freeze dryer for 2 days
  7. additionThe solid was then suspended in a mixture of MeOH (60 ml) and Et2O (200 ml)
  8. filtrationfiltered
  9. washThe solid was washed with additional Et2O (2×100 ml)
  10. customplaced in a round bottom flask in vacuo overnight

Sources & evidence

ORD record
ord-4b6e793ea2c1424aae2ff51c4e66c55b
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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