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Cesium carbonate → (S)-3-((S)-3-(4-(4-Bromo-3-(trifluoromethoxy)benzyloxy)-phenyl)-3-(isoxazol-3-yl)propanoyl)-4-benzyloxazolidin-2-one

HRID 1675265
Notes
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Reaction equation

HRID 1675265 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].S(Br)(Br)=O.[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](O)=[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+]>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:43]2[CH:42]=[CH:41][C:40]([C@@H:34]([C:35]3[CH:39]=[CH:38][O:37][N:36]=3)[CH2:33][C:32]([N:27]3[C@@H:26]([CH2:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:30][O:29][C:28]3=[O:31])=[O:47])=[CH:45][CH:44]=2)=[CH:4][C:3]=1[O:10][C:11]([F:13])([F:12])[F:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 68176Thionyl bromideHCID 54472733(4-Bromo-3-(trifluoromethoxy)phenyl)methanolHCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

Product 1

HCID 59300650(S)-3-((S)-3-(4-(4-Bromo-3-(trifluoromethoxy)benzyloxy)-phenyl)-3-(isoxazol-3-yl)propanoyl)-4-benzyloxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 28.3 (1.30 g, 4.80 mmol), thionyl bromide (1.01 g, 4.84 mmol), and DMF (0.1 mL) in DCM (8.0 mL) was stirred at room temperature for 50 minutes. The solvent was then removed. To the residue was added 7.5 (1.10 g, 2.80 mmol) and Cs2CO3 (1.10 g, 3.36 mmol) in DMF (8.0 mL). The mixture was stirred at room temperature for 4 hours. EtOAc (150 mL) was added, and the mixture was washed with brine (25×3 mL) and dried with MgSO4. The solvent was removed, and the crude product was purified by CombiFlash, eluting with EtOAc and hexane, to give the title compound 28.4. 1H NMR (CDCl3) δ 2.77 (dd, J=4.2, 9.5 Hz, 1 H), 3.21 (dd, J=4.2, 9.5 Hz, 1 H), 3.52 (dd, J=8.6, 17.6 Hz, 1 H), 4.04 (dd, J=8.6, 17.6 Hz, 1 H), 4.63 (m, 1 H), 4.76 (m, 1 H), 5.01 (s, 2 H), 6.14 (d, J=1.5 Hz, 1 H), 6.92 (d, J=6.9,Hz, 2 H), 7.20-7.35 (m, 9 H), 7.64 (d, J=8.3,Hz, 1H), 8.31 (d, J=1.5 Hz, 1 H). MS ESI (pos.) m/e: 647 (M+H).

Workup

  1. customThe solvent was then removed
  2. stirringThe mixture was stirred at room temperature for 4 hours
  3. washthe mixture was washed with brine (25×3 mL)
  4. dry with materialdried with MgSO4
  5. customThe solvent was removed
  6. customthe crude product was purified by CombiFlash
  7. washeluting with EtOAc and hexane

Sources & evidence

ORD record
ord-4ad66d2857774da1a770f3fabec82fbc
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08003648B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes