Cesium carbonate → HCID 20812491, compound

HRID 895803Notes

Reaction equation

HRID 895803 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C@@:8]2([F:24])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:21]Cl)[C:9]2=[O:23])[CH:7]=1.[CH2:27]([O:34][C@@H:35]1[C@@H:41]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@H:40]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C@@H:39]([CH2:58][O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[O:38][CH:36]1[OH:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C@@:8]2([F:24])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:19])([F:18])[F:20])=[CH:14][CH:15]=3)[N:10]([CH2:21][O:37][CH:36]3[C@H:35]([O:34][CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C@@H:41]([O:42][CH2:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C@@H:40]([O:50][CH2:51][C:52]4[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=4)[C@@H:39]([CH2:58][O:59][CH2:60][C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[O:38]3)[C:9]2=[O:23])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranoseHCID 86593818HCID 86593818, compound

Product 1

HCID 20812491HCID 20812491, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a round bottom flask containing a solution of (S)-3-(5-Chloro-2-methoxy-phenyl)-1-chloromethyl-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one (S)-IV) (0.486 g, 1.2 mmol) in anhydrous acetonitrile (9 mL) was added 2,3,4,6-tetra-O-benzyl-D-glucopyranose (V; 0.648 g, 1.2 mmol) and cesium carbonate (0.390 g, 1.2 mmol). The reaction mixture was allowed to stir at room temperature overnight. The solvent was then removed, and the crude product was purified via flash chromatography (silica gel, 5:1 hexanes:ethyl acetate) to give a 1:1 mixture of α and β anomers of the title compound (0.768 g, 71%). 1H NMR (CDCl3, 400 MHz): δ 7.79 (dd, 2H, J=5.1 Hz, 1.8 Hz), 7.37-7.12 (m, 48H), 6.66 (m, 2H), 5.66 (d, 1H, J=11.0 Hz), 5.34 (m, 2H), 5.08 (d, 1H, J=3.7 Hz), 4.89-4.73 (m, 9H), 4.66-4.44 (m, 9H), 3.79 (m, 3H), 3.73-3.59 (m, 6H), 3.55-3.49 (m, 3H), 3.38 (d, 6H, J=4.1 Hz).

Workup

  1. customThe solvent was then removed
  2. customthe crude product was purified via flash chromatography (silica gel, 5:1 hexanes:ethyl acetate)
  3. customto give

Sources & evidence

ORD record
ord-2b61c5ac0a5a434086b6220c43b847ee
Source dataset
uspto-grants-2005_07
Patent number
US06916937B2

Reaction notes

Loading…