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

HRID 1675317Notes

Reaction equation

HRID 1675317 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[CH:6][C:7]=1[CH3:8].[CH2:19]([C@H:26]1[CH2:30][O:29][C:28](=[O:31])[N:27]1[C:32](=[O:47])[CH2:33][C@@H:34]([C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=1)[C:35]1[CH:39]=[CH:38][O:37][N:36]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[O:37]1[CH:38]=[CH:39][C:35]([C@H:34]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:2][C:3]3[S:4][C:5]([C:9]4[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=4)=[CH:6][C:7]=3[CH3:8])=[CH:42][CH:41]=2)[CH2:33][C:32]([N:27]2[C@@H:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:30][O:29][C:28]2=[O:31])=[O:47])=[N:36]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 159462812-(Chloromethyl)-3-methyl-5-[4-(trifluoromethyl)phenyl]thiopheneHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

Product 1

HCID 59300606(4S)-3-((3S)-3-(3-Isoxazolyl)-3-(4-(((3-methyl-5-(4-(trifluoromethyl)phenyl)-2-thienyl)methyl)oxy)phenyl)propanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-oneYield 76.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 62.7 (0.23 mmol), 7.5 (76 mg, 0.19 mmol), and Cs2CO3 (226 mg, 0.69 mmol) in DMF (2.3 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 (15-45% EtOAc/hexane) to afford 62.8 (94 mg, 75%) as a white solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was chromatographed on silica gel (15-45% EtOAc/hexane)

Sources & evidence

ORD record
ord-ad1aaa2bf09b486ebd4bff2e7a8a7b72
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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