Hydrochloric Acid → (2R)-4-{4'-[(5R)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2'-fluorobiphenyl-4-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 533561Notes

Reaction equation

HRID 533561 reaction equation
Cl.[C:2]([NH:5][CH2:6][C@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C@@:27]([CH3:42])([S:38]([CH3:41])(=[O:40])=[O:39])[C:28]([NH:30][O:31]C4CCCCO4)=[O:29])=[CH:21][CH:20]=3)=[C:15]([F:43])[CH:14]=2)[CH2:8]1)(=[O:4])[CH3:3]>O1CCOCC1.ClCCl.O>[C:2]([NH:5][CH2:6][C@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][C@@:27]([CH3:42])([S:38]([CH3:41])(=[O:40])=[O:39])[C:28]([NH:30][OH:31])=[O:29])=[CH:23][CH:24]=3)=[C:15]([F:43])[CH:14]=2)[CH2:8]1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86668777(2R)-4-{4'-[(5R)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2'-fluorobiphenyl-4-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86668778(2R)-4-{4'-[(5R)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2'-fluorobiphenyl-4-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Reagents, catalysts & solvents 1

HCID 866687791,4 Dioxane dichloromethane waterSolvent

Procedure

HCl (4.0 M in 1,4-dioxane, 1.0 mL) was added to a solution of (2R)-4-{4′-[(5R)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2′-fluorobiphenyl-4-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (50 mg, 0.083 mmol) in 1,4 dioxane/dichloromethane/water (1:1:1, 3 mL). After 15 minutes reaction was concentrated to give a white solid. The solid was triturated with a mixture of diethyl ether/2-propanol (10:1, 10 mL) for 2 hours. The title compound was collected as a white solid (16 mg, 37%) by filtration. LCMS m/z 522.6 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (s, 3H) 1.84 (s, 3H) 1.88-1.98 (m, 1H) 2.37-2.48 (m, 1H) 2.63-2.76 (m, 2H) 3.05 (s, 3H) 3.43 (t, J=5.47 Hz, 2H) 3.78 (dd, J=9.28, 6.35 Hz, 1H) 4.17 (t, J=8.98 Hz, 1H) 4.70-4.82 (m, 1H) 7.34 (d, J=8.20 Hz, 2H) 7.40 (dd, J=8.49, 2.25 Hz, 1H) 7.45-7.51 (m, 2H) 7.51-7.62 (m, 2H) 8.26 (t, J=5.86 Hz, 1H).

Workup

  1. customAfter 15 minutes reaction
  2. concentrationwas concentrated
  3. customto give a white solid
  4. customThe solid was triturated with a mixture of diethyl ether/2-propanol (10:1, 10 mL) for 2 hours
  5. filtrationThe title compound was collected as a white solid (16 mg, 37%) by filtration

Sources & evidence

ORD record
ord-8f619a928c114cd59627e643fc579613
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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