Cesium carbonate → HCID 86695668, compound

HRID 594751Notes

Reaction equation

HRID 594751 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH:9]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[C:12](=[O:26])[CH:11]([OH:27])[CH2:10]1.[F:28][CH2:29][CH2:30]I.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:30][CH2:29][F:28])[C:3]=1[CH:9]1[N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]([F:24])([F:25])[F:23])=[CH:19][CH:20]=2)[C:12](=[O:26])[CH:11]([OH:27])[CH2:10]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 69082672HCID 69082672, compound

Product 1

HCID 86695668HCID 86695668, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of rac-(3R*,5S*)-5-(2-fluoro-6-hydroxyphenyl)-3-hydroxy-1-(4-(trifluoromethoxy)benzyl)pyrrolidin-2-one (50 mg; 0.13 mmol), 1-fluoro-2-iodoethane (23 mg; 0.13 mmol), potassium carbonate (36 mg; 0.26 mmol), and cesium carbonate (8.5 mg; 0.026 mmol) in anh. DMF (1.3 ml) was stirred at rt, under nitrogen, for 72 h. Filtration of the reaction mixture, and subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.79 min.; [M+H]+: 431.96 g/mol.

Workup

  1. filtrationFiltration of the reaction mixture, and subsequent purification by preparative HPLC
  2. customafforded the target compound

Sources & evidence

ORD record
ord-724557980fd54b8da20a9a22df55315e
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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