Hydrochloric Acid → HCID 56646839, compound

HRID 71254Notes

Reaction equation

HRID 71254 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]3[N:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]4([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:33][CH2:32][CH2:31][CH2:30][C:25]54OCC[O:26]5)[O:18][N:17]=3)=[CH:11][C:10]=2[CH3:40])[CH2:4][O:3]1.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[OH:6][C@@H:5]([CH2:4][OH:3])[CH2:7][O:8][C:9]1[C:10]([CH3:40])=[CH:11][C:12]([C:16]2[N:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]3([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:33][CH2:32][CH2:31][CH2:30][C:25]3=[O:26])[O:18][N:17]=2)=[CH:13][C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 666928363-(4-(((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3,5-dimethylphenyl)-5-(3-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)propyl)-1,2,4-oxadiazole

Product 1

HCID 56646839HCID 56646839, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-(4-(((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3,5-dimethylphenyl)-5-(3-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)propyl)-1,2,4-oxadiazole (57 mg, 0.101 mmol) in acetic acid (1 mL) was added 1N HCl (0.2 mL, 0.200 mmol), and the mixture was stirred at 0° C. for 1.5 hrs. The mixture was poured into saturated Na2CO3 and the product was extracted with EtOAc (2×). The combined extracts were washed with brine, dried over Na2SO4 and evaporated to give an oily residue. The residue was purified by Combiflash (24 g silica gel) eluting with 1:1 followed by 7:3 EtOAc-hexane, to afford 2-(3-(3-(4-((S)-2,3-dihydroxypropoxy)-3,5-dimethylphenyl)-1,2,4-oxadiazol-5-yl)propyl)-2-phenylcyclohexanone as a solid (34.4 mg). LC/MS: m/e 479.1 (M+H)+. 1H NMR (400 MHz, CCl3D) δ ppm 7.67 (2H, s), 7.31-7.38 (2H, m), 7.24 (1H, t, J=7.25 Hz), 7.14 (2H, d, J=7.47 Hz), 4.06-4.15 (2H, m), 3.75-3.90 (5H, m), 2.70-2.81 (3H, m), 2.26-2.38 (8H, m), 1.84-1.97 (2H, m), 1.59-1.78 (6H, m), 1.37-1.52 (1H, m).

Workup

  1. extractionthe product was extracted with EtOAc (2×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customto give an oily residue
  6. customThe residue was purified by Combiflash (24 g silica gel)
  7. washeluting with 1:1

Sources & evidence

ORD record
ord-a73a18b5b3504dc19121f02ef6ebc636
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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