Hydrochloric Acid → HCID 68109155, compound

HRID 2179403Notes

Reaction equation

HRID 2179403 reaction equation
C([C:3]1([C:33]([O-:35])=O)[C:8]2[C:9]3[CH:15]=[C:14]([S:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)(=[O:18])=[O:17])[CH:13]=[C:12]([Cl:25])[C:10]=3[O:11][C:7]=2[CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O)C.Cl.[C:37](=[O:40])(O)[O-].[Na+].Cl[CH2:43]Cl>O1CCOCC1>[Cl:25][C:12]1[C:10]2[O:11][C:7]3[CH2:6][CH2:5][NH:4][CH:3]([C:33]([O:40][CH2:37][CH3:43])=[O:35])[C:8]=3[C:9]=2[CH:15]=[C:14]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 86668005HCID 86668005, compound

Product 1

HCID 68109155HCID 68109155, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of the product of step C (60 mg, 0.12 mmol) in dichloromethane (2 mL) was added 4M HCl in dioxane (2 mL). The resulting solution was stirred at ambient temperature for 3 h. The solvents were removed in vacuo to afford a brown residue which was treated with saturated aqueous sodium bicarbonate (15 mL). The resulting solution was extracted with ethyl acetate (3×15 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 4:2 to 3:7, hexanes/ethyl acetate) to afford ethyl 6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-1-carboxylate (51 mg, 99%) as a brown oil: 1H NMR (CDCl3, 300 MHz) δ 8.23 (d, J=1.8 Hz, 1H), 7.97-7.85 (m, 2H), 7.70-7.57 (m, 4H), 4.76 (s, 1H), 4.27-4.17 (m, 2H), 3.77-3.63 (m, 2H), 3.42-3.22 (m, 1H), 2.98-2.76 (m, 1H), 1.28 (t, J=7.2 Hz, 3H).

Workup

  1. customThe solvents were removed in vacuo
  2. customto afford a brown residue which
  3. extractionThe resulting solution was extracted with ethyl acetate (3×15 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 4:2 to 3:7, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-fb129472eda842c7a2dfc19f2c07c936
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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