HCID 68004074, compound → (1H-Indol-3-ylsulfanyl)-acetic acid

HRID 1621270Notes

Reaction equation

HRID 1621270 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][CH2:11][C:12]([O:14]C)=[O:13])=[CH:2]1>O1CCCC1.[Li+].[OH-].ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:2]1

Participants

5

Reactant 1

HCID 68004074HCID 68004074, compound

Product 1

HCID 590707(1H-Indol-3-ylsulfanyl)-acetic acidYield 38%

Reagents, catalysts & solvents 3

HCID 3939Lithium HydroxideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-((1H-indol-3-yl)thio)acetate from Step A was dissolved in a mixture of tetrahydrofuran (20 mL) and 2.0 M aqueous LiOH (15 mL), then stirred vigorously at ambient temperature for 30 min. Tetrahydrofuran was removed in vacuo, the aqueous layer neutralized with 1.2 N HCl and extracted with CH2Cl2. The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo to produce an oily residue. Upon diluting the residue in dichloromethane a solid formed which was filtered and dried to yield the desired product (2.00 grams, 9.65 mmol, 38% yield over 2 steps). LCMS>99% at 254 nm, RT=1.02 min, m/z=208 (M+1).

Workup

  1. customTetrahydrofuran was removed in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto produce an oily residue
  6. customformed which
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-7081289dd766440c83c3699322d7769c
Source dataset
uspto-grants-2014_07
Patent number
US08772509B2

Reaction notes

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