Sodium Hydroxide → HCID 118377835, compound

HRID 1055509Notes

Reaction equation

HRID 1055509 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]23[O:15][C@:12]([CH:16]([OH:23])[C:17]#[C:18][Si](C)(C)C)([CH2:13][O:14]2)[C@@H:11]([OH:24])[C@H:10]([OH:25])[C@H:9]3[OH:26])=[CH:4][C:3]=1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH3:36])=[CH:30][CH:29]=1.[OH-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]23[O:15][C@:12]([CH:16]([OH:23])[C:17]#[CH:18])([CH2:13][O:14]2)[C@@H:11]([OH:24])[C@H:10]([OH:25])[C@H:9]3[OH:26])=[CH:4][C:3]=1[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][CH3:36])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 131736382HCID 131736382, compound

Product 1

HCID 118377835HCID 118377835, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S,2S,3S,4R,5S)-5-[4-chloro-3 [(4-ethoxyphenyl)methyl]phenyl]-1-(1-hydroxy-3-trimethysilyl-prop-2-ynyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 4b (0.44 g, 0.82 mmol) in anhydrous methanol (20 mL) was added sodium hydroxide (32.9 mg, 8.2 mmol). The mixture was stirred at room temperature for 10 hours. The reaction mixture was adjusted to pH 6-7 with saturated aqueous ammonium chloride, and extracted with ethyl acetate (40 mL×3). The combined organic layers were washed with water (30 mL×2) and then saturated aqueous sodium chloride (20 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by prep-HPLC to give the title compound 4 (56 mg, 14.7%, HPLC: 84.2%) as colorless oil. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 461.1[M+H]+; and 1H NMR (400 MHz, DMSO-d6) δ(ppm): 7.41 (m, 2H), 7.31 (m, 1H), 7.09 (d, 2H), 6.83 (d, 2H), 5.69 (d, 1H), 5.37 (d, 1H), 5.06 (d, 1H), 4.97 (d, 1H), 4.45 (m, 2H), 3.97 (m, 5H), 3.81 (s, 1H), 3.77 (d, 1H), 3.76 (t, 1H), 3.51 (m, 1H), 1.29 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (40 mL×3)
  2. washThe combined organic layers were washed with water (30 mL×2)
  3. dry with materialsaturated aqueous sodium chloride (20 mL×2), dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-0d649700ff514138b5518f115ebeec4c
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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