HCID 90177793, compound → HCID 90177037, compound

HRID 1499293Notes

Reaction equation

HRID 1499293 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([S:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH2:28][C:29]2[CH:34]=[CH:33][C:32](/[CH:35]=[CH:36]/[CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:31][CH:30]=2)[CH:22]=1)(=[O:3])[CH3:2]>C1COCC1.CO.[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([S:19][CH3:20])[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:33][CH:34]=2)[CH:22]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 90177793HCID 90177793, compound

Product 1

HCID 90177037HCID 90177037, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(2S,3S,4R,5S,6R)-2-(3-(4-((E)-4-methoxy-4-oxobut-1-en-1-yl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (8, 1.74 g, 3.0 mmol) was dissolved in a 1:1 (v:v) THF/MeOH solution. Pd/C (10% wet, 174 mg) was added and the reaction hydrogenated at 40 psi for 3 hours. The reaction was monitored by 1H NMR. Upon completion, the reaction was filtered over Celite with excess MeOH. Removal of solvents in vacuo provided the product as a light yellow solid (1.65 g, 94% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.11-7.20 (m, 2 H), 7.07 (t, J=7.8 Hz, 3 H), 6.99 (d, J=8.1 Hz, 2 H), 5.33 (dd, J=9.6 Hz, 1 H), 5.21 (dd, J=9.6 Hz, 1 H), 5.12 (dd, J=9.6 Hz, 1 H), 4.52 (d, J=9.9 Hz, 1 H), 4.39 (d, J=9.9 Hz, 1 H), 3.85-4.00 (m, 2 H), 3.67 (s, 3 H), 2.61 (t, J=7.6 Hz, 2H), 2.33 (t, J=7.5 Hz, 2 H), 2.21 (s, 3 H), 2.18 (s, 3 H), 2.10 (s, 3 H), 2.01 (s, 3 H), 1.93 (quin, J=7.6 Hz, 2 H), 1.75 (s, 3 H). MS (ES+) [M+NH4]+=604.

Workup

  1. customthe reaction hydrogenated at 40 psi for 3 hours
  2. filtrationUpon completion, the reaction was filtered over Celite with excess MeOH
  3. customRemoval of solvents in vacuo

Sources & evidence

ORD record
ord-139df80bdb7e4d33bbba582653100444
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Reaction notes

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