Cesium fluoride → HCID 86604964, compound

HRID 1714011Notes

Reaction equation

HRID 1714011 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-].[Cs+].[N+](C1C=C(S(O[CH2:42][C@H:43]2[O:45][CH2:44]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH2:42][C@@H:43]2[CH2:44][O:45]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 11995228Methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1H-indole-6-carboxylate

Product 1

HCID 86604964HCID 86604964, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the foregoing product from Step 1 in DMF (0.04 M) were added cesium fluoride (3 eq) and (S)-glycidyl 3-nitrobenzenesulfonate (1.1 eq). The resulting mixture was stirred at RT overnight, then diluted with EtOAc and washed with water and brine. Drying over Na2SO4, filtration and concentration in vacuo gave the crude product, which was purified by flash chromatography on silica gel (1:5 EtOAc/PE) to afford the title compound as a colourless foam (74%); MS (ES+) m/z 406 (M+H)+; [α]D20=+22 (c=0.5, CHCl3).

Workup

  1. washwashed with water and brine
  2. dry with materialDrying over Na2SO4, filtration and concentration in vacuo
  3. customgave the crude product, which
  4. customwas purified by flash chromatography on silica gel (1:5 EtOAc/PE)

Sources & evidence

ORD record
ord-e87b1f62be7f490598b72dbe34bff232
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

Loading…