HCID 86685162, compound → HCID 86685163, compound

HRID 1913066Notes

Reaction equation

HRID 1913066 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@@:12]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[C:35]([CH2:40][C:41]3[S:42][C:43]([C:46]4[CH:51]=[CH:50][C:49]([F:52])=[CH:48][CH:47]=4)=[CH:44][CH:45]=3)[CH:34]=2)([O:31]C)[O:11][C:10]1([CH2:55]O)[CH2:53][OH:54])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[F:52][C:49]1[CH:48]=[CH:47][C:46]([C:43]2[S:42][C:41]([CH2:40][C:35]3[CH:34]=[C:33]([C@@:12]45[O:11][C@@:10]([CH2:53][OH:54])([CH2:55][O:31]4)[C@@H:9]([OH:8])[C@H:14]([OH:15])[C@H:13]5[OH:23])[CH:38]=[CH:37][C:36]=3[CH3:39])=[CH:45][CH:44]=2)=[CH:51][CH:50]=1

Participants

5

Reactant 1

HCID 86685162HCID 86685162, compound

Product 1

HCID 86685163HCID 86685163, compoundYield 13.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 9j (130 mg, 0.17 mmol) was dissolved in 10 mL methanol, followed by addition of a solution (4 mL) of 2 M hydrochloric in ethyl acetate and Palladium/carbon (260 mg, 20%). The mixture was exchanged with H2 three times and stirred for 16 hours. Thereafter, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by HPLC to obtain the title compound (1S,2S,3S,4R,5S)-5-[3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methyl-phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 9 (11 mg, white solid), yield: 13.8%. MS m/z (ESI): 473.2 [M+1]; 1H NMR (400 MHz, CD3OD): δ 7.57-7.56 (m, 2H), 7.48 (d, 1H), 7.39-7.37 (m, 1H), 7.19 (d, 1H), 7.15 (d, 1H), 7.10-7.06 (m, 2H), 6.67 (d, 1H), 4.18 (d, 3H), 3.88-3.81 (m, 2H), 3.73-3.68 (m, 2H), 3.65-3.62 (m, 2H), 2.33 (s, 3H).

Workup

  1. filtrationThereafter, the reaction mixture was filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-e039f4df77eb45448d40ed365464b418
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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