Lithium Hydroxide → HCID 25168567, compound

HRID 1175301Notes

Reaction equation

HRID 1175301 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][CH:38]([OH:41])[CH2:39][OH:40])[O:7][C@@H:6]1[CH2:42][O:43]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]([CH2:42][OH:43])[O:7]2)=[C:20]([CH2:35][O:36][CH2:37][CH:38]([OH:41])[CH2:39][OH:40])[CH:21]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68743780HCID 68743780, compound

Product 1

HCID 25168567HCID 25168567, compoundYield 9.3%

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-2-((2,3-dihydroxypropoxy)methyl)-5-(4-ethylbenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (50 mg, 0.076 mmol) (prepared from intermediate J using a Sharpless dihydroxylation) 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 3.5 mg of pure product as a white solid. 1H-NMR (CD3OD, 300 MHz) δ 7.45 (s, 1H), 7.43 (s, 1H), 7.08 (s, 4H), 4.75-4.70 (m, 2H), 4.60-4.45 (m, 2H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.93-3.83 (m, 2H), 3.87-3.77 (m, 2H), 3.66-3.36 (m, 7H), 2.60 (q, J=7.8 Hz, 2H), 1.21 (t, J=7.8 Hz, 3H), 1.15 (d, J=7.8 Hz, 3H); LC-MS (m/z) 497 [(M+1)+], 541 [(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-01ad757e3ea349adb95d4e969ee25aba
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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