Acetic Acid → HCID 11283696, compound

HRID 915287Notes

Reaction equation

HRID 915287 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].[C:33]([OH:36])(=[O:35])[CH3:34].CCOCC>C([O-])(=O)C.[Hg+2].C([O-])(=O)C.O>[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:36][C:33](=[O:35])[CH3:34])[CH3:3])=[O:32])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 58958558HCID 58958558, compound

Product 1

HCID 11283696HCID 11283696, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 962WaterSolvent

Procedure

Acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin 5(R)-ylmethyl}-carbamic acid 1(R,S)-chloro-ethyl ester (11) (0.49 g, 1 mmol), mercury(II) acetate (0.37 g, 1.175 mmol), and acetic acid (6.3 mL, 109 mmol) are stirred at RT overnight. Ether and water are added and the layers are separated. The organic layer is washed several times with water, brine, dried over Na2SO4 and conc in vacuo. After purification by silica gel chromatography, the product is re-dissolved in CH2Cl2 and washed with several portions of sat NaHCO3, water, dried over Na2SO4 and conc in vacuo to give the title compound in 43% yield (0.51 g) as a mixture of two diastereomers in a 1:1 ratio. 1H NMR (400 MHz, CDCl3): δ 7.46 (dt, 1H), 7.21 (m, 1H), 7.13 (m, 1H), 6.88 (q, 1H), 4.82 (m, 0.5H), 4.75 (m, 0.5H), 4.13 (m, 1H), 4.04 (m, 2H), 3.73 (dd, 0.5H), 3.67 (dd, 0.5H), 3.12 (m, 5H), 2.55 (s, 1.5H), 2.53 (s, 1.5H), 2.38 (m, 2H), 2.17 (m, 2H), 2.13 (s, 1.5H), 2.06 (s, 1.5H), 1.57 (d, 1.5H), 1.54 (d, 1.5H). MS-APCI (m/z+): 341, 385, 427, 515.

Workup

  1. customthe layers are separated
  2. washThe organic layer is washed several times with water, brine
  3. dry with materialdried over Na2SO4 and conc in vacuo
  4. customAfter purification by silica gel chromatography
  5. dissolutionthe product is re-dissolved in CH2Cl2
  6. washwashed with several portions of sat NaHCO3, water
  7. dry with materialdried over Na2SO4 and conc in vacuo

Sources & evidence

ORD record
ord-b22a746944d24f00b1f1b32f4cebadf0
Source dataset
uspto-grants-2007_09
Patent number
US07265140B2

Reaction notes

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