Hydrochloric Acid → HCID 44354897, compound

HRID 1167497Notes

Reaction equation

HRID 1167497 reaction equation
Cl.[S:2]1[N:6]=[CH:5][C:4]([O:7][CH2:8][C@@H:9]2[O:13][C:12](=[O:14])[N:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH2:26][CH2:25][N:24]([C:27]([C@@H:29]5[CH2:33][O:32]C(C)(C)[O:30]5)=[O:28])[CH2:23][CH:22]=4)=[C:17]([F:36])[CH:16]=3)[CH2:10]2)=[N:3]1>C1COCC1>[S:2]1[N:6]=[CH:5][C:4]([O:7][CH2:8][C@@H:9]2[O:13][C:12](=[O:14])[N:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH2:26][CH2:25][N:24]([C:27](=[O:28])[C@@H:29]([OH:30])[CH2:33][OH:32])[CH2:23][CH:22]=4)=[C:17]([F:36])[CH:16]=3)[CH2:10]2)=[N:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69980858HCID 69980858, compound

Product 1

HCID 44354897HCID 44354897, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1N aqueous HCl (1 ml) was added to a solution of 5(R)-(1,2,5-thiadiazol-3-yloxymethyl)-3-(3-fluoro4-(1-(2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)phenyl)oxazolidin-2-one (0.154 g, 0.32 mmol) in THF (3 ml) and the solution kept for two days. The solution was evaporated and the residue azeotroped twice with ethanol. The residue was purified by chromatography on a BondElut silica column, eluting first with dichloromethane and then 2% MeOH/dichloromethane to give the title product (37 mg, 26%) as a solid. MS: 465 (MH+); NMR(400 MHz): 2.5 (2H+DMSO); 3.3 (1H, s)3.4 (1H, m); 3.5 (1H, m); 3.76 (1H, m); 4.0 (1H, t); 4.15 (1H, s); 4.26 (1H, t); 4.4 (1H, m); 4.8 (3H, m); 4.97 (1H, m); 5.18 (1H, m); 6.03 (1H, s); 7.32-7.46 (2H, m); 7.53 (1H, d); 8.47 (1H, s).

Workup

  1. customThe solution was evaporated
  2. customthe residue azeotroped twice with ethanol
  3. customThe residue was purified by chromatography on a BondElut silica column
  4. washeluting first with dichloromethane

Sources & evidence

ORD record
ord-43cba6f312654c2f9a61adb5fb5c9e53
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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