HCID 59557700, compound → HCID 25168848, compound

HRID 1175314Notes

Reaction equation

HRID 1175314 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@H:12]([C:31]2[CH:36]=[C:35]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][CH:39]=3)[C:34]([Cl:46])=[CH:33][C:32]=2[CH2:47][CH2:48][O:49][CH2:50][C:51]([F:54])([F:53])[F:52])[O:11][C@@H:10]1[CH2:55][O:56]CC1C=CC=CC=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[Cl:46][C:34]1[C:35]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44][CH3:45])=[CH:40][CH:39]=2)=[CH:36][C:31]([C@H:12]2[C@H:13]([OH:23])[C@@H:14]([OH:15])[C@H:9]([OH:8])[C@@H:10]([CH2:55][OH:56])[O:11]2)=[C:32]([CH2:47][CH2:48][O:49][CH2:50][C:51]([F:54])([F:52])[F:53])[CH:33]=1

Participants

4

Reactant 1

HCID 59557700HCID 59557700, compound

Product 1

HCID 25168848HCID 25168848, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of (2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-5-(4-ethylbenzyl)-2-(2-(2,2,2-trifluoroethoxy)ethyl)phenyl)tetrahydro-2H-pyran (30 mg, 0.034 mmol) and 10% Pd/C (30 mg) in 6 mL of MeOH:THF (1:1) was stirred under H2 atmosphere (1 atm) for 2 h. The mixture was filtered, and the filtrate was concentrated to provide the crude product, which was purified by HPLC to yield 9 mg of title compound. 1H-NMR (CD3OD, 300 MHz) δ 7.40 (s, 1H), 7.27 (s, 1H), 7.10 (s, 4H), 4.44-4.41 (m, 1H), 4.06 (d, J=15.3 Hz, 1H), 4.00 (d, J=15.3 Hz, 1H), 3.95-3.79 (m, 5H), 3.67-3.61 (m, 1H), 3.48-3.46 (m, 2H), 3.39-3.36 (m, 2H), 3.15-3.05 (m, 1H), 2.98-2.91 (m, 1H), 2.58 (q, J=7.6 Hz, 2H), 1.19 (t, J=7.6 Hz, 3H); MS ESI (m/z) 519 (M+1)+, calc. 518.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto provide the crude product, which
  4. customwas purified by HPLC

Sources & evidence

ORD record
ord-6627b689b7d04d27bdd01dc426f50c32
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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