Cesium carbonate → (4S)-3-((3S)-3-(4-(((5-(4-butylphenyl)-2-thienyl)methyl)oxy)phenyl)-3-(3-isoxazolyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

HRID 1675304Notes

Reaction equation

HRID 1675304 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[CH2:18]([C@H:25]1[CH2:29][O:28][C:27](=[O:30])[N:26]1[C:31](=[O:46])[CH2:32][C@@H:33]([C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[C:34]1[CH:38]=[CH:37][O:36][N:35]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[S:4][C:3]([CH2:2][O:45][C:42]3[CH:43]=[CH:44][C:39]([C@@H:33]([C:34]4[CH:38]=[CH:37][O:36][N:35]=4)[CH2:32][C:31]([N:26]4[C@@H:25]([CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH2:29][O:28][C:27]4=[O:30])=[O:46])=[CH:40][CH:41]=3)=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-oneHCID 593006792-(4-Butylphenyl)-5-(chloromethyl)thiophene

Product 1

HCID 59300558(4S)-3-((3S)-3-(4-(((5-(4-butylphenyl)-2-thienyl)methyl)oxy)phenyl)-3-(3-isoxazolyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-oneYield 32.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 60.5 (0.16 mmol), 7.5 (52 mg, 0.13 mmol), and Cs2CO3 (135 mg, 0.41 mmol) in DMF (1.6 mL) was stirred overnight at room temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), and concentrated. The crude product was chromatographed on silica gel (0-30% EtOAc/hexane) to afford 60.6 (26 mg, 32%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 8.29 (d, 1H), 7.48 (d, 2H), 7.28 (m, 5H), 7.19 (m, 4H), 7.14 (d, 1H), 7.04 (d, 1H), 6.96 (d, 2H), 6.13 (d, 1H), 5.17 (s, 2H), 4.75 (t, 1H), 4.61 (m, 1H), 4.13 (m, 2H), 4.02 (dd, 1H), 3.54 (dd, 1H), 3.20 (dd, 1H), 2.76 (dd, 1H), 2.62 (t, 2H), 1.61 (m, 2H), 1.37 (m, 2H), 0.94 (t, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (0-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-03a1080e52854b0cb4e9d921f6e5c7a6
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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