Hydrochloric Acid → HCID 68485442, compound

HRID 1874942Notes

Reaction equation

HRID 1874942 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](C(OCCC(C)(C)C)=O)[C:10]([C:24]([O-:26])=[O:25])=[CH:9]2.Cl.[CH2:28]1COC[CH2:29]1>O1CCOCC1>[CH3:1][S:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:24]([O:26][CH2:28][CH3:29])=[O:25])=[CH:9]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 86761646HCID 86761646, compound

Product 1

HCID 68485442HCID 68485442, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(1,1-dimethylethyl)2-ethyl 5-{[2-(methylthio)ethyl]oxy}-1H-indole-1,2-dicarboxylate (0.500 g, 1.31 mmol) in THF was treated with 4 M HCl in dioxane and stirred for 5 hours. The solvent was evaporated to an oil and the residue was dissolved in DCM and TFA was added and stirred until no starting material remained as evident by TLC. The mixture was evaporated to a solid and purification was accomplished by silica gel column chromatography (0-50% EtOAc/hexanes) to afford the title compound (0.228 g, 61%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 9.21-9.37 (m, 1H), 7.32 (d, 1H), 7.12-7.16 (m, 1H), 7.09 (d, 1H), 7.00 (dd, 1H), 4.42 (q, 2H), 4.19 (t, 2H), 2.91 (t, 2H), 2.22 (s, 3H), 1.42 (t, 3H). LCMS: m/z=279.9 (M+1).

Workup

  1. customThe solvent was evaporated to an oil
  2. dissolutionthe residue was dissolved in DCM
  3. additionTFA was added
  4. stirringstirred until no starting material
  5. customThe mixture was evaporated to a solid and purification

Sources & evidence

ORD record
ord-1d7b89aeeecb400ea456049a68c16783
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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