Hydrochloric Acid → HCID 44354903, compound

HRID 1167487Notes

Reaction equation

HRID 1167487 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:27][C@H:26]([CH2:28][O:29][C:30]5[CH:34]=[CH:33][O:32][N:31]=5)[O:25][C:24]4=[O:35])=[CH:19][C:18]=3[F:36])=[CH:13][CH2:12]2)=[O:10])[CH2:4][O:3]1.Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][C@H:26]([CH2:28][O:29][C:30]4[CH:34]=[CH:33][O:32][N:31]=4)[O:25][C:24]3=[O:35])=[CH:19][C:18]=2[F:36])=[CH:13][CH2:12]1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57218104HCID 57218104, compound

Product 1

HCID 44354903HCID 44354903, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylmethoxycarbonyl)-1,2,5,6-tetrahydro-4-pyridinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (130 mg, 0.25 mmol) was dissolved in tetrahydrofuran (5 ml), treated with 2 M aqueous hydrochloric acid (2 ml), and stirred at ambient temperature for 72 hours. Excess potassium carbonate was added to remove acid and water, and the solution filtered. The filtrate was evaporated, and the residue purified by chromatography on a 10 g silica Biotage column, eluting with a gradient increasing in polarity from 0 to 10% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (103 mg). MS (ESP): 478 (MH+) for C22H24FN3O8.

Workup

  1. customto remove acid and water
  2. filtrationthe solution filtered
  3. customThe filtrate was evaporated
  4. customthe residue purified by chromatography on a 10 g silica Biotage column
  5. washeluting with a gradient
  6. temperatureincreasing in polarity from 0 to 10% MeOH in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-7b5b19e617764cae9d06d2f9f9bec6f9
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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