Acetic Acid → HCID 117985974, compound

HRID 1055623Notes

Reaction equation

HRID 1055623 reaction equation
C([O:4][C@H:5]1[C@H:11](CC([O-])=O)[C@@H:10]([O:16]C(=O)C)[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH:36]([O:38]C(=O)C)[CH3:37])CO2)(=O)C.[CH3:42][O-:43].[Na+].C(O)(=[O:47])C>CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C@@:9]23[O:20][C@@:6]([CH:36]([OH:38])[CH3:37])([CH2:42][O:43]2)[C@@H:5]([OH:4])[C@H:11]([OH:47])[C@H:10]3[OH:16])=[CH:22][C:23]=1[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 131736408HCID 131736408, compound

Product 1

HCID 117985974HCID 117985974, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(1R,2S,3S,4R,5S)-2,4-diacetoxy-1-(1-acetoxyethyl)-5-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-3-yl]acetate 31b (1.17 g, 1.98 mmol) in methanol (20 mL) was added sodium methoxide (85 mg, 1.57 mmol) at rt. The mixture was stirred at rt for 4 hours, and then acetic acid (0.1 mL) was added. The resulting mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluted with EtOAc to give the title compound 31c as a white foam (0.78 g, 93.2%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, MeOD) δ(ppm): 7.44 (d, 1H), 7.42-7.34 (m, 2H), 7.03 (d, 2H), 6.70 (d, 2H), 4.17 (d, 1H), 4.06-3.98 (m, 3H), 3.92 (d, 1H), 3.78 (d, 1H), 3.66 (t, 1H), 3.55 (d, 1H), 1.33 (d, 3H).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel chromatography
  3. washeluted with EtOAc

Sources & evidence

ORD record
ord-a08f6fc8b02a4bacaa4f7721752bc1c6
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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