Hydrochloric Acid → HCID 58124911, compound

HRID 1971644Notes

Reaction equation

HRID 1971644 reaction equation
[C:1]([N:5]([CH2:13][CH2:14][C:15]#[C:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:6](=[O:12])[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].Cl>O1CCOCC1.O>[C:1]([N:5]([CH2:13][CH2:14][C:15]#[C:16][C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:6](=[O:12])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58124846HCID 58124846, compound

Product 1

HCID 58124911HCID 58124911, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 100 mg of 1d in 1 ml of dioxane was mixed with a solution of 40 mg of KOH in 400 μl of water and stirred for 16 hr at RT. The mixture was diluted with 5 ml of water and acidified to pH3 with 0.5 N HCl. The product was extracted with ethyl acetate and the extracts were washed once with sat. NaCl, dried and concentrated, to provide 65 mg of essentially pure 1e as colorless oil; MS-ESI: [M+1] 280.16; NMR (CDCl3) δ 1.54 (s, 9, tertC4H9), 2.80 (m, 2, CH2), 4.10 (bm, 2, CH2), 6.94, 7.13, 7.20 (3×m, 3, thiophene-H).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe extracts were washed once with sat. NaCl
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cfd0ca4b89b64f9c9903e867501a6167
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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