Sodium Iodide → HCID 11331321, compound

HRID 915288Notes

Reaction equation

HRID 915288 reaction equation
Cl[CH2:2][O:3][C:4](=[O:31])[N:5]([C:28](=[O:30])[CH3:29])[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]3)=[C:15]([F:27])[CH:14]=2)[CH2:8]1.[I-].[Na+].[Cs].[C:35]([N:42]1[CH2:50][CH2:49][CH:45]([C:46]([OH:48])=[O:47])[CH2:44][CH2:43]1)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C(#N)C>[C:38]([O:37][C:35]([N:42]1[CH2:50][CH2:49][CH:45]([C:46]([O:48][CH2:2][O:3][C:4](=[O:31])[N:5]([C:28](=[O:30])[CH3:29])[CH2:6][C@@H:7]2[O:11][C:10](=[O:12])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]4)=[C:15]([F:27])[CH:14]=3)[CH2:8]2)=[O:47])[CH2:44][CH2:43]1)=[O:36])([CH3:41])([CH3:39])[CH3:40]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 5354618CesiumHCID 58958555HCID 58958555, compound

Product 1

HCID 11331321HCID 11331321, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (R)-acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid chloromethyl ester (10) (751.8 mg, 1.58 mmol) and sodium iodide (236.0 mg, 1.58 mmol) in acetonitrile (30 mL), is added the cesium salt of N-BOC-isonipecotic acid (884.2 mg, 2.45 mmol). The mixture is heated to reflux overnight. After cooling to RT, the mixture is filtered and washed with dichloromethane. The filtrate is diluted with CH2Cl2 and water and the layers are separated. The aq layer is extracted with dichloromethane twice and the combined organic layers are washed with water, brine, dried over sodium sulfate and conc in vacuo. Purification by silica gel chromatography gave the title compound in 72% yield (757.3 mg, 1.13 mmol). 1H NMR (400 MHz, CDCl3): δ 7.47 (dd, 1H), 7.24 (t, 1H), 7.14 (dd, 1H), 5.88 (s, 2H), 4.78-4.85 (m, 1H), 4.18 (dd, 1H), 4.08 (t, 2H), 4.03 (dd, 2H), 3.67 (dd, 1H), 3.13-3.20 (m, 4H), 3.10 (dt, 1H), 2.83 (t, 2H), 2.60 (tt, 1H), 2.59 (s, 3H), 2.35-2.46 (m, 2H), 2.17-2.23 (m, 2H), 1.90-1.96 (m, 2H), 1.57-1.686 (m, 2H) 1.45 (s, 9H). MS-APCI (m/z+): 570.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. filtrationthe mixture is filtered
  4. washwashed with dichloromethane
  5. additionThe filtrate is diluted with CH2Cl2 and water
  6. customthe layers are separated
  7. extractionThe aq layer is extracted with dichloromethane twice
  8. washthe combined organic layers are washed with water, brine
  9. dry with materialdried over sodium sulfate and conc in vacuo
  10. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-2264161bb69e4f4ba47f5eee1133f0ec
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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