HCID 86593819, compound → HCID 69736214, compound

HRID 895807Notes

Reaction equation

HRID 895807 reaction equation
C([O:8][C@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([CH2:23][O:24]CC2C=CC=CC=2)[O:12][C@@H:11]([N:32]2[C:40]3[C:35](=[CH:36][CH:37]=[C:38]([C:41]([F:44])([F:43])[F:42])[CH:39]=3)[C@@:34]([C:46]3[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=3[O:53][CH3:54])([F:45])[C:33]2=[O:55])[C@@H:10]1[O:56][P:57](=[O:74])([O:66]CC1C=CC=CC=1)[O:58]CC1C=CC=CC=1)C1C=CC=CC=1>[Pt]=O.C(OCC)(=O)C>[Cl:52][C:50]1[CH:49]=[CH:48][C:47]([O:53][CH3:54])=[C:46]([C@@:34]2([F:45])[C:35]3[C:40](=[CH:39][C:38]([C:41]([F:44])([F:42])[F:43])=[CH:37][CH:36]=3)[N:32]([C@H:11]3[C@H:10]([O:56][P:57](=[O:58])([OH:66])[OH:74])[C@@H:9]([OH:8])[C@H:14]([OH:15])[C@@H:13]([CH2:23][OH:24])[O:12]3)[C:33]2=[O:55])[CH:51]=1

Participants

4

Reactant 1

HCID 86593819HCID 86593819, compound

Product 1

HCID 69736214HCID 69736214, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask containing Phosphoric acid dibenzyl ester 4-(S),5-(S)-bis-benzyloxy-6-(R)-benzyloxymethyl-2-(R)-[3-(S)-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indol-1-yl]-tetrahydro-pyran-3-(R)-yl ester (3-(S)-IX) (0.117 g, 0.11 mmol) was added ethyl acetate (1 mL). Platinum oxide (0.013 g, 0.06 mmol) was added to the reaction mixture which was then placed under a hydrogen atmosphere. The reaction was allowed to stir at room temperature overnight. The crude reaction mixture was purified via reverse phase column chromatography (C18, 1:1 water:acetonitrile). The title product was obtained as a white solid (0.045 g, 68%). 1H NMR (MeOH-D4, 400 MHz): δ 7.72 (d, 1H, J=1.8 Hz), 7.5 (s, 1H), 7.38 (dd, 1H, J=6.2 Hz, 2.6 Hz), 7.29 (dd, 1H, J=21.7 Hz, 7.7 Hz), 6.93 (dd, 1H, J=7.7 Hz, 1.1 Hz), 5.61 (d, 1H, J=9.4 Hz), 3.97 (d, 1H, J=11.9 Hz), 3.77 (m, 2H), 3.57 (s, 3H); 19F NMR (MeOH-D4, 376 MHz): δ−64.5, −163.3; 31P NMR (MeOH-D4, 161 MHz): δ 1.54; LRMS: 599 [M−H]−.

Workup

  1. customThe crude reaction mixture
  2. customwas purified via reverse phase column chromatography (C18, 1:1 water:acetonitrile)

Sources & evidence

ORD record
ord-937b397d4ff04fd590e72977efb5c896
Source dataset
uspto-grants-2005_07
Patent number
US06916937B2

Reaction notes

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