Lithium Hydroxide → HCID 70873250, compound

HRID 1022471Notes

Reaction equation

HRID 1022471 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]([CH:21]3[CH2:23][CH2:22]3)=[C:17]([CH2:24][C:25]3[CH:34]=[CH:33][C:28]4[O:29][CH2:30][CH2:31][O:32][C:27]=4[CH:26]=3)[CH:16]=2)[O:8][CH:7]([S:35][CH3:36])[C@H:6]1[O:37]C(=O)C)(=O)C.[OH-].[Li+]>CO.C1COCC1.O>[CH:21]1([C:18]2[CH:19]=[CH:20][C:15]([C@H:9]3[C@H:10]([OH:11])[C@@H:5]([OH:4])[C@H:6]([OH:37])[CH:7]([S:35][CH3:36])[O:8]3)=[CH:16][C:17]=2[CH2:24][C:25]2[CH:34]=[CH:33][C:28]3[O:29][CH2:30][CH2:31][O:32][C:27]=3[CH:26]=2)[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86691701HCID 86691701, compound

Product 1

HCID 70873250HCID 70873250, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Step-XI: To a stirred solution of acetic acid (3S,4R,5S,6S)-4,5-diacetoxy-6-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-2-methylsulfanyl-tetrahydro-pyran-3-yl ester (80 mg, 0.14 mmol) in methanol:THF:water (3:2:1 mixture, 6 ml) was added lithium hydroxide (9 mg, 0.4 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 55 mg of (2S,3R,4R,5S)-2-[4-cyclopropyl-3-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenyl]-6-methylsulfanyl-tetrahydro-pyran-3,4,5-triol. 1H NMR (400 MHz, CD3OD): δ 0.52-0.60 (m, 2H), 0.80-0.90 (m, 2H), 1.78-1.88 (m, 1H), 2.15 (s, 3H), 3.32-3.35 (m, 3H), 4.05 (q, J=15.2 Hz, 2H), 4.11 (d, J=8.8 Hz, 1H), 4.17 (s, 4H), 4.38 (d, J=10 Hz, 1H), 6.61 (d, J=8.0 Hz, 2H), 6.69 (d, J=8.4 Hz, 1H), 6.98 (d, J=8.0 Hz, 1H), 7.15 (d, J=7.6 Hz, 1H), 7.17 (d, J=8.0 Hz, 1H). MS (ES) m/z 462.3 (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-9b4c53bb0abf4859a5875d07fc0462ee
Source dataset
uspto-grants-2014_05
Patent number
US08722633B2

Reaction notes

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