Lithium hydroxide, monohydrate → HCID 25168845, compound

HRID 1175311Notes

Reaction equation

HRID 1175311 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][CH2:36][O:37][CH2:38][CH2:39][OH:40])[O:7][C@@H:6]1[CH2:41][O:42]C(=O)C)(=O)C.O[Li].O>C1COCC1.CO.O>[Cl:34][C:22]1[C:23]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH3:33])=[CH:30][CH:31]=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]([CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40])[CH:21]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59557723HCID 59557723, compound

Product 1

HCID 25168845HCID 25168845, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-5-(4-ethylbenzyl)-2-(2-(2-hydroxyethoxy)ethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (31 mg, 0.048 mmol) in THF:MeOH:H2O (2:3:1, 0.6 mL) was added LiOH—H2O (2.8 mg, 0.067 mmol). After being stirred overnight at room temperature, the reaction mixture was concentrated. The residue was dissolved in EtOAc, washed 1× with brine, 1× with brine containing 1% NaHSO4 and 1× with brine prior to drying over Na2SO4. Concentration gave 22 mg of title compound. 1H-NMR (CD3OD, 300 MHz) δ 7.38 (s, 1H), 7.27 (s, 1H), 7.07 (s, 4H), 4.47 (dd, J=9.6, 3.0 Hz, 1H), 4.02 (s, 2H), 3.85 (d, J=12.3 Hz, 1H), 3.71-3.62 (m, 5H), 3.53-3.46 (m, 4H), 3.39-3.37 (m, 2H), 3.13-3.03 (m, 1H), 2.97-2.87 (m, 1H), 2.58 (q, J=7.5 Hz, 2H), 1.19 (t, J=7.5 Hz, 3H); MS ESI (m/z) 481 (M+1)+, calc. 480.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed 1× with brine, 1× with brine containing 1% NaHSO4 and 1× with brine
  4. dry with materialto drying over Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-f3449dc2579e49c8817c714806e97640
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

Loading…