Lithium Hydroxide → HCID 66562317, compound

HRID 1022473Notes

Reaction equation

HRID 1022473 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[C:17]([CH2:23][C:24]3[CH:33]=[CH:32][C:27]4[O:28][CH2:29][CH2:30][O:31][C:26]=4[CH:25]=3)[CH:16]=2)[O:8][CH:7]([O:34][CH3:35])[C@H:6]1[O:36]C(=O)C)(=O)C.[OH-].[Li+]>CO.C1COCC1.O>[O:28]1[C:27]2[CH:32]=[CH:33][C:24]([CH2:23][C:17]3[CH:16]=[C:15]([C@H:9]4[C@H:10]([OH:11])[C@@H:5]([OH:4])[C@H:6]([OH:36])[C@@H:7]([O:34][CH3:35])[O:8]4)[CH:20]=[CH:19][C:18]=3[CH2:21][CH3:22])=[CH:25][C:26]=2[O:31][CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86691702HCID 86691702, compound

Product 1

HCID 66562317HCID 66562317, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Step-IV: To a stirred solution of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-2-methoxy-tetrahydro-pyran-3-yl ester (300 mg, 0.55 mmol) in methanol:THF:water (3:2:1 mixture, 6 ml) was added lithium hydroxide (46 mg, 1.10 mmol). After stirring for 2 h at room temperature, volatiles were evaporated under reduced pressure. The resulting residue was taken in ethyl acetate (10 ml) and washed with brine (5 ml), brine containing 1 ml of 5% aqueous KHSO4 (5 ml), brine (5 ml), dried over sodium sulfate, concentrated and purified by preparative HPLC to furnish 90 mg (2S,3R,4R,5S,6S)-2-[3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-4-ethyl-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol as white solid. 1H NMR (400 MHz, CD3OD): δ 0.56-0.58 (m, 2H), 0.84-0.87 (m, 2H), 1.80-1.85 (m, 1H), 3.27-3.44 (m, 3H), 3.48 (s, 3H), 4.05 (d, J=6.4 Hz, 2H), 4.10 (d, J=9.3 Hz, 1H), 4.17 (s, 4H), 4.30 (d, J=7.8 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H), 6.69 (d, J=8.4 Hz, 2H), 6.98 (d, J=7.8 Hz, 1H), 7.16-7.19 (m, 2H). MS (ES) m/z 446.3 (M+18).

Workup

  1. customvolatiles were evaporated under reduced pressure
  2. washwashed with brine (5 ml), brine containing 1 ml of 5% aqueous KHSO4 (5 ml), brine (5 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-71fe1b95d3b0446d95fde098765c16ac
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

Loading…