Acetic Acid → HCID 18442996, compound

HRID 459054Notes

Reaction equation

HRID 459054 reaction equation
C(O[C:6]([N:8](C)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][C@H:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([N:34]4[CH2:38][C@H:37]([CH2:39][N:40]5[CH:44]=[CH:43][N:42]=[N:41]5)[O:36][C:35]4=[O:45])=[CH:30][C:29]=3[F:46])=[CH:24][N:23]=2)[CH2:18]1)=[O:14])=O)(C)(C)C.C(O)(=O)C.Cl>CO>[CH3:6][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][C@H:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][C:31]([N:34]4[CH2:38][C@H:37]([CH2:39][N:40]5[CH:44]=[CH:43][N:42]=[N:41]5)[O:36][C:35]4=[O:45])=[CH:30][C:29]=3[F:46])=[CH:24][N:23]=2)[CH2:18]1)=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 58758436HCID 58758436, compound

Product 1

HCID 18442996HCID 18442996, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

[(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 5-[(tert-butoxycarbonyl)(methyl)amino]pentanoate (Example 34: 0.5 g, 0.77 mmol) was combined with acetic acid (15 ml) and hydrochloric acid (4M solution in dioxane, 1 ml, 4 mmol). The suspension was warmed for 2 minutes at approximately 80° C. to dissolve most of the suspended material. The mixture was stirred at room temperature for an additional 15 minutes then concentrated under reduced pressure. The residual solids were dissolved in water (40 ml) then extracted twice with ethyl acetate (20 ml). Evaporation of the aqueous layer followed by drying under reduced pressure gave a solid that was dissolved in methanol (1 ml) and precipitated by the addition of diethyl ether (10 ml). The solution was decanted off and the precipitation was repeated. The resulting sticky oil was dried in vacuo at 50° C. to give the hydrochloride salt of the title compound as a hygroscopic solid (0.46 g), melting point: 184° C.

Workup

  1. dissolutionto dissolve most of the suspended material
  2. concentrationthen concentrated under reduced pressure
  3. dissolutionThe residual solids were dissolved in water (40 ml)
  4. extractionthen extracted twice with ethyl acetate (20 ml)
  5. customEvaporation of the aqueous layer
  6. customby drying under reduced pressure
  7. customgave a solid
  8. customprecipitated by the addition of diethyl ether (10 ml)
  9. customThe solution was decanted off
  10. customthe precipitation
  11. customThe resulting sticky oil was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-a6b4210800fd4ec8ac20b2cb89de2159
Source dataset
uspto-grants-2007_03
Patent number
US07192974B2

Reaction notes

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