Lithium Hydroxide → HCID 76071002, compound

HRID 1499294Notes

Reaction equation

HRID 1499294 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[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]([CH2:35][CH2:36][CH2:37][C:38]([O:40]C)=[O:39])=[CH:31][CH:30]=2)[CH:22]=1)(=O)C.[OH-].[Li+].OS([O-])(=O)=O.[Na+]>CO.C1COCC1.O>[CH3:27][C:24]1[CH:25]=[CH:26][C:21]([C@H:6]2[C@H:5]([OH:4])[C@@H:10]([OH:11])[C@H:9]([OH:15])[C@@H:8]([S:19][CH3:20])[O:7]2)=[CH:22][C:23]=1[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516919Sodium BisulfateHCID 90177037HCID 90177037, compound

Product 1

HCID 76071002HCID 76071002, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

(2S,3S,4R,5S,6R)-2-(3-(4-(4-methoxy-4-oxobutyl)benzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (9, 1.65 g, 2.81 mmol) was dissolved in a MeOH/THF/H2O solution (25 mL, 2:1:2 vol. ratio). Lithium hydroxide (674 mg, 28.1 mmol) was added and the reaction stirred at room temperature for 1 hour. The reaction was acidified to pH=1-2 with saturated aqueous NaHSO4. The acidic aqueous layer was extracted three times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude product was rotovapped down once from hexanes to provide the product as white transferable solid (1.27 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.99 (s, 1 H), 6.96-7.16 (m, 7H), 5.16 (d, J=5.8 Hz, 1 H), 5.06 (d, J=4.3 Hz, 1 H), 4.82 (d, J=5.6 Hz, 1 H), 4.32 (d, J=9.6 Hz, 1H), 4.04 (d, J=9.1 Hz, 1 H), 3.90 (s, 2 H), 2.53 (t, J=7.3 Hz, 2 H), 2.19 (t, J=7.3 Hz, 2 H), 2.17 (s, 3H), 2.03 (s, 3 H), 1.76 (quin, J=7.6 Hz, 2 H). MS (ES+) [M+NH4]+=464.

Workup

  1. extractionThe acidic aqueous layer was extracted three times with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51caea83802b49e9981e3c13010626da
Source dataset
uspto-grants-2015_12
Patent number
US09200025B2

Reaction notes

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