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Sodium Iodide → HCID 11445358, compound

HRID 915295
Notes
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Reaction equation

HRID 915295 reaction equation
Cl[CH:2]([O:4][C:5](=[O:32])[N:6]([C:29](=[O:31])[CH3:30])[CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]3)=[C:16]([F:28])[CH:15]=2)[CH2:9]1)[CH3:3].[Cs].[C:34]([NH:41][C@H:42]([C:47]([OH:49])=[O:48])[C@H:43]([CH2:45][CH3:46])[CH3:44])([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[I-].[Na+]>O.C(#N)C>[C:29]([N:6]([CH2:7][C@@H:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:25][CH2:24][S:23](=[O:27])(=[O:26])[CH2:22][CH2:21]3)=[C:16]([F:28])[CH:15]=2)[CH2:9]1)[C:5]([O:4][CH:2]([O:49][C:47](=[O:48])[C@@H:42]([NH:41][C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@@H:43]([CH3:44])[CH2:45][CH3:46])[CH3:3])=[O:32])(=[O:31])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 2724762tert-Butoxycarbonyl-L-isoleucineHCID 5354618CesiumHCID 58958558HCID 58958558, compound

Product 1

HCID 11445358HCID 11445358, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6342AcetonitrileSolvent

Procedure

Acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5(R)-ylmethyl}-carbamic acid 1-chloro-ethyl ester (11) (1.00 g, 2.04 mmol), the cesium salt of N-BOC-L-isoleucine (15f) (1.48 g, 4.07 mmol), sodium iodide (0.31 g, 2.07 mmol) and acetonitrile (50 mL) are heated to reflux overnight. After cooling to RT, water is added and the reaction mixture is extracted with EtOAc and then with dichloromethane. The organic phases are washed separately with brine and then the organic layers are combined, dried over MgSO4, filtered, and conc in vacuo. The isolated residue is subjected to silica gel flash chromatography, eluting with MeOH/CH2Cl2 gradient (0-4% MeOH over 1 hour and 30 minutes) to afford the title compound. Isolated yield: 79%. 1H NMR (400 MHz, CDCl3): δ 7.48-7.42 (m, 1H), 7.22-7.17 (m, 1H), 7.14-7.10 (m, 1H), 6.91-6.85 (m, 1H), 5.08 (d, 0.5H), 4.94 (d, 0.5H), 4.81-4.74 (m, 1H), 4.24-3.98 (m, 4H), 3.71-3.64 (m, 1H), 3.13-3.04 (m, 5H), 2.51 (d, 3H), 2.42-2.31 (m, 2H), 2.17-2.13 (m, 2H), 1.84-1.81 (br m, 1H), 1.57 (dd, 3H), 1.52 (s, 1H), 1.38 (d, 9H), 1.21-1.09 (m, 1H), 0.93-0.85 (m, 6H); MS-APCI (m/z+): 341, 385, 586, 686.

Workup

  1. temperatureto reflux overnight
  2. extractionthe reaction mixture is extracted with EtOAc
  3. washThe organic phases are washed separately with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. washeluting with MeOH/CH2Cl2 gradient (0-4% MeOH over 1 hour and 30 minutes)

Sources & evidence

ORD record
ord-57343c5487504a5297fbfb6e53e2dd40
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07265140B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes