Cesium carbonate → HCID 66750799, compound

HRID 504152Notes

Reaction equation

HRID 504152 reaction equation
Br[CH2:2][CH2:3][CH2:4][F:5].[CH2:6]([O:13][C:14](=[O:43])[C@@H:15]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=1)(=[O:35])=[O:34])=[O:26])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:6]([O:13][C:14](=[O:43])[C@@H:15]([NH:24][C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=1)(=[O:35])=[O:34])=[O:26])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:2][CH2:3][CH2:4][F:5])=[CH:19][CH:18]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 59428654HCID 59428654, compound2×

Product 1

HCID 66750799HCID 66750799, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-1-fluoro propane (1.6 g, 11 mmol) was added to a mixture of (S)-2-{[(S)-1-(3-fluoro-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-3-(4-hydroxy-phenyl)-propionic acid benzyl ester (compound 17c) (2.0 g, 3.7 mmol) and cesium carbonate (3.6 g, 11 mmol) in DMF (60 mL). The suspension was stirred overnight at room temperature. The reaction mixture was diluted in ethyl acetate and washed with water, dried over magnesium sulfate and concentrated. The resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel to produce 1.89 g (85.1%) of the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resulting oil was chromatographed (dichloromethane/methanol, 9/1) on silica gel

Sources & evidence

ORD record
ord-4a58dd68efb04a84ba1899eac4483ad2
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

Loading…