Cesium carbonate → HCID 58758897, compound

HRID 2375738Notes

Reaction equation

HRID 2375738 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]Cl)[CH:15]=2)=[C:10]([CH3:22])[CH:9]=1.[OH:23][C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]([C:37]2[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=2)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:26][CH:25]=1>CN(C=O)C.CCOC(C)=O>[CH2:35]([O:34][C:32](=[O:33])[CH2:31][C@@H:30]([C:27]1[CH:26]=[CH:25][C:24]([O:23][CH2:20][C:16]2[CH:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][C:10]=3[CH3:22])[CH:19]=[CH:18][CH:17]=2)=[CH:29][CH:28]=1)[C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=1)[CH3:36]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 59855115HCID 59855115, compoundHCID 59855123HCID 59855123, compound

Product 1

HCID 58758897HCID 58758897, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cs2CO3 (72 mg, 0.22 mmol) and compound 9.9 (53 mg, 0.21 mmol) were added successively to a solution of (S)-ethyl 3-(4-hydroxyphenyl)-3-(1-methyl-1H-imidazol-2-yl)propanoate (9.6) (55 mg, 0.2 mmol) in dry DMF (3 mL). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc (60 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue was flash chromatographed on silica gel (0-5% MeOH in DCM) to afford (S)-ethyl 3-(4-[3-(4-chloro-2-methylphenyl)benzyloxy]phenyl)-3-(1-methyl-1H-imidazol-2-yl)propanoate (9.10) as a colorless oil (97 mg). LC-MS ESI (pos.) m/e: 489 (M+H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customchromatographed on silica gel (0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-7659b7b29aa6416aa67ab576012cf520
Source dataset
uspto-grants-2008_12
Patent number
US07465804B2

Reaction notes

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