Triethylamine → HCID 44242680, compound

HRID 1446071Notes

Reaction equation

HRID 1446071 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][C@H:9]([O:13][CH2:14][C:15]#[CH:16])[CH2:8][O:7]2)([O-:3])=[O:2].[F:17][C:18]1[CH:19]=[C:20]([N:25]2[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]2=[O:35])[CH:21]=[CH:22][C:23]=1I.CCN(CC)CC>[Cu]I.CN(C=O)C>[F:17][C:18]1[CH:19]=[C:20]([N:25]2[CH2:29][C@H:28]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[O:27][C:26]2=[O:35])[CH:21]=[CH:22][C:23]=1[C:16]#[C:15][CH2:14][O:13][C@@H:9]1[CH2:8][O:7][C:6]2=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]2[CH2:10]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11222662(S)-N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamideHCID 44818302HCID 44818302, compound

Product 1

HCID 44242680HCID 44242680, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To an oven dried round bottom flask was charged 2-Nitro-6(S)-prop-2-ynyloxy-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (75 mg, 0.34 mmol), N-[3-(3-Fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]-acetamide (127 mg, 0.34 mmol), PhCl2(PPh3)2 (23 mg, 0.02 mmol) and CuI (3.2 mg, 0.017 mmol). The flask was flushed with nitrogen before degassed DMF (4 mL) and Et3N (0.15 mL, 1.05 mmol) were added. The resultant mixture was stirred at 80° C. for one hour before it was cooled down and partitioned into 50 mL EtOAc/50 mL water. The organic layer was washed with brine and dried over Na2SO4. Column chromatography (CH2Cl2/MeOH, v/v, 20:1 to 10:1) of the concentrated residue gave the titled compound (60 mg) as yellow solid. ESI MS m/z 474 (M+H). 1H NMR (400 MHz, MeCN-d3) 7.73 (s, 1H), 7.65 (dd, J=12.4, 2.4 Hz, 1H), 7.59 (t, J=8.4 Hz, 1H), 7.39 (dd, J=8.8, 2.4 Hz, 1H), 6.84 (b, 1H), 4.20-4.99 (m, 1H), 4.76 (dt, J=12.4, 2.8 Hz, 1H), 4.67 (s, 2H), 4.53 (d, J=12.8 Hz, 1H), 4.45-4.51 (m, 1H), 4.26-4.42 (m, 2H), 4.17 (t, J=9.2 Hz, 1H), 3.85 (dd, J=9.6, 5.2 Hz, 1H), 3.56-3.68 (m, 2H), 1.98 (s, 3H).

Workup

  1. customTo an oven dried round bottom flask
  2. customThe flask was flushed with nitrogen
  3. additionwere added
  4. temperaturewas cooled down
  5. custompartitioned into 50 mL EtOAc/50 mL water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-503800c06dd6486fa2087bd6ff0cc0fa
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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