Ethanol → HCID 9937468, compound

HRID 895804Notes

Reaction equation

HRID 895804 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:64][CH3:65])=[C:6]([C@@:8]2([F:63])[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][O:22][CH:23]3[C@H:28]([O:29]CC4C=CC=CC=4)[C@@H:27]([O:37]CC4C=CC=CC=4)[C@@H:26]([O:45]CC4C=CC=CC=4)[C@@H:25]([CH2:53][O:54]CC4C=CC=CC=4)[O:24]3)[C:9]2=[O:62])[CH:7]=1.C(O)C>[Pt]=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:64][CH3:65])=[C:6]([C@@:8]2([F:63])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=3)[N:10]([CH2:21][O:22][CH:23]3[C@H:28]([OH:29])[C@@H:27]([OH:37])[C@H:26]([OH:45])[C@@H:25]([CH2:53][OH:54])[O:24]3)[C:9]2=[O:62])[CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 20812491HCID 20812491, compound

Product 1

HCID 9937468HCID 9937468, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask containing a solution of 3-(S)-(5-Chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1-(3-(R),4-(S),5-(S)-tris-benzyloxy-6-(R)benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-1,3-dihydro-indol-2-one; (3-(S)-VI) (0.768 g, 0.84 mmol) in 1:1 ethanol:ethyl acetate (6 mL) was added platinum oxide (0.095 g, 0.42 mmol). The reaction was allowed to run at room temperature under a hydrogen atmosphere for 6 days. Once complete, the reaction was filtered through a bed of celite and purified via reverse phase column chromatography (C18, 1:1 water:acetonitrile). The title compound was isolated as a white solid (0.279 g, 60%). 1H NMR (MeOH-D4, 400 MHz): δ 7.74 (m, 2H), 7.59 (d, 2H, J=8.8 Hz), 7.41 (m, 4H), 7.30 (dd, 2H, J=5.5 Hz, 2.3 Hz), 6.96 (m, 2H), 5.62 (d, 1H, J=10.8 Hz), 5.55 (d, 1H, J=11.3 Hz), 5.48 (d, 1H, J=10.8 Hz), 5.39 (d, 1H, J=11.2 Hz), 5.07 (d, 1H, J=3.8 Hz), 4.50 (d, 1H, J=7.8 Hz), 3.87 (dd, 1H, J=10 Hz, 1 Hz), 3.68 (m, 4H), 3.54 (d, 6H, J=2.6 Hz), 3.51 (d, 1H, J=4.6 Hz), 3.45 (d, 1H, J=3.8 Hz), 3.43 (d, 1H, J=3.8 Hz), 3.38 (m, 1H), 3.33 (m, 2H), 3.24 (m, 1H ); LRMS: 569 [M+NH4]+.

Workup

  1. filtrationOnce complete, the reaction was filtered through a bed of celite and
  2. custompurified via reverse phase column chromatography (C18, 1:1 water:acetonitrile)

Sources & evidence

ORD record
ord-7c1ec675989b445f8fa4ba0d820aacbd
Source dataset
uspto-grants-2005_07
Patent number
US06916937B2

Reaction notes

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