Lithium Hydroxide → HCID 25168566, compound

HRID 1175300Notes

Reaction equation

HRID 1175300 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]([C:19]2[CH:24]=[C:23]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=3)[C:22]([Cl:34])=[CH:21][C:20]=2[CH2:35][O:36][CH2:37][C:38](=[O:40])[CH3:39])[O:7][C@@H:6]1[CH2:41][O:42]C(=O)C)(=O)C.[OH-].[Li+]>C1COCC1.CO.O>[Cl:34][C:22]1[C:23]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH3:33])=[CH:28][CH:27]=2)=[CH:24][C:19]([C@H:8]2[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:41][OH:42])[O:7]2)=[C:20]([CH:21]=1)[CH2:35][O:36][CH2:37][C:38](=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68744663HCID 68744663, compound

Product 1

HCID 25168566HCID 25168566, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-5-(4-ethylbenzyl)-2-((2-oxopropoxy)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (36.8 g, 0.057 mmol) (prepared from intermediate J using a Wacker oxidation as described for the preparation of intermediate T-1 below) in THF:MeOH:H2O (2:3:1, 1.2 mL) was added lithium hydroxide (3.71 mg). The reaction was stirred overnight at 20° C. The volatiles were removed and the residue was dissolved in EtOAc (20 mL), washed 1× with brine, 1× with brine containing 2 mL of 5% aqueous KHSO4 and dried over Na2SO4. Concentration gave 16 mg of pure product as a white solid. 1H-NMR (CD3OD, 300 MHz) δ 7.47 (s, 1H), 7.44 (s, 1H), 7.08 (s, 4H), 4.80 (d, J=12.3 Hz, 1H), 4.55 (d, J=9.6 Hz, 1H), 4.22 (s, 2H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.85 (dd, J=11.7 Hz, 2.1 Hz, 1H), 387-3.83 (m, 1H), 3.68-3.63 (m, 1H), 3.50-3.36 (m, 4H), 2.58 (q, J=7.8 Hz, 2H), 2.12 (s, 3H), 1.19 (t, J=7.8 Hz, 3H); LC-MS (m/z) 479 [(M+1)+], 523 [(M+45)−].

Workup

  1. customThe volatiles were removed
  2. dissolutionthe residue was dissolved in EtOAc (20 mL)
  3. washwashed 1× with brine, 1× with brine containing 2 mL of 5% aqueous KHSO4
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-78278f95cf7d4309a7155b3b5203034d
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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