(S)-N-((3-(3-fluoro-4-Morpholinophenyl)-2-oxooxazolidin-5-yl)Methyl)ethanethioaMide → HCID 53751722, compound

HRID 279060Notes

Reaction equation

HRID 279060 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:21](NC)=[S:22])[O:16][C:15]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.FC1C=C(N2C[C@H](CNC(=S)C)OC2=O)C=CC=1N1CCOCC1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][CH:21]=[S:22])[O:16][C:15]2=[O:25])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 12040041(S)-N-((3-(3-fluoro-4-Morpholinophenyl)-2-oxooxazolidin-5-yl)Methyl)ethanethioaMideHCID 59953075HCID 59953075, compound

Product 1

HCID 53751722HCID 53751722, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 6 (0.38 g, 0.00118 mol) in dioxane (20 mL), under nitrogen was treated with 4 (0.51 g, 0.00126 mol), warmed to reflux during 30 min and kept at this temperature for 90 min. It was then evaporated under a stream of nitrogen. The residue was chromatographed on silica gel with 1.25% MeOH—CH2Cl2 and the slightly impure product was rechromatographed on silica gel with 25% EtOAc-CH2Cl2. The resulting product was crystallized from EtOAc-methyl tert-butyl ether to give 0.114 g of 7: mp 150-155° C. (dec.); IR (DRIFT) 3322, 1752 cm−1; MS(ES) m/z 340 (M+H+), 362 (M+Na+); 1HNMR [300 MHz, (CD3)2SO] d 2.94 (m, 4H), 3.72 (m, 4H), 3.77 (d,d, 1H), 3.94 (t, 2H), 4,12 (t, 1H), 4.93 (m, 1H), 7.05 (t, 1), 7.16 (d,d, 1H), 7.47 (d,d, 1H), 9.33 (d, 1H), 10.59 (s, 1H), Anal. cald for C15H18FN3O3S: C, 53.08; H, 5,35; N, 12.38. Found: C, 53.02; H, 5.44; N, 12.36.

Workup

  1. temperaturewarmed
  2. temperatureto reflux during 30 min
  3. customIt was then evaporated under a stream of nitrogen
  4. customThe residue was chromatographed on silica gel with 1.25% MeOH—CH2Cl2
  5. customthe slightly impure product was rechromatographed on silica gel with 25% EtOAc-CH2Cl2
  6. customThe resulting product was crystallized from EtOAc-methyl tert-butyl ether

Sources & evidence

ORD record
ord-c1f7211cafca4a6cb6a43baca8d184ac
Source dataset
uspto-grants-2002_03
Patent number
US06362189B1

Reaction notes

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