Lithium hydroxide, monohydrate → HCID 25168565, compound

HRID 1175299Notes

Reaction equation

HRID 1175299 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]=[CH2:39])[O:7][C@@H:6]1[CH2:40][O:41]C(=O)C)(=O)C.O[Li].O>C1COCC1.CO.O>[CH2:37]([O:36][CH2:35][C:20]1[CH:21]=[C:22]([Cl:34])[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]=1[C@H:8]1[C@H:9]([OH:15])[C@@H:10]([OH:11])[C@H:5]([OH:4])[C@@H:6]([CH2:40][OH:41])[O:7]1)[CH:38]=[CH2:39]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59557680HCID 59557680, compound

Product 1

HCID 25168565HCID 25168565, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(2-(allyloxymethyl)-4-chloro-5-(4-ethylbenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (246 mg, 0.39 mmol) in THF:MeOH:H2O (2:3:1, 6 mL) was added LiOH.H2O (16.4 mg, 0.47 mmol). After being stirred for 12 h at room temperature, the reaction mixture was concentrated and the residue was dissolved in 20 mL of EtOAc. The organic layer was washed with brine and dried over Na2SO4 Concentration gave a residue, which was purified by preparative TLC (PE:EtOAc:MeOH=8:80:1, Rf=0.5) to yield 132 mg of title compound as a white solid. 1H-NMR (CD3OD, 400 MHz) δ 7.48 (s, 1H), 7.42 (s, 1H), 7.11 (s, 4H), 5.93-5.87 (m, 1H), 5.24 (dd, J=17.2 Hz, 1.6 Hz, 1H), 5.11 (dd, J=1.6 Hz, 10.4 Hz, 1H), 4.85 (d, J=12.0 Hz, 1H), 4.62 (d, J=12.0 Hz, 1H), 4.51 (d, J=9.2 Hz, 1H), 4.23 (s, 2H), 4.10 (d, J=14.8 Hz, 1H), 4.05 (d, J=14.8 Hz, 1H), 3.88 (d, J=12.4 Hz, 1H), 3.71-3.67 (m, 1H), 3.52-3.41 (m, 4H), 2.60 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); LC-MS (m/z) 463 [(M+1)+], 507 [(M+45)−].

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in 20 mL of EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4 Concentration
  5. customgave a residue, which
  6. customwas purified by preparative TLC (PE:EtOAc:MeOH=8:80:1, Rf=0.5)

Sources & evidence

ORD record
ord-f93f4cbf66e34c7e9148db4f09a6ca29
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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