Acrylic Acid → HCID 19921623, compound

HRID 1463316Notes

Reaction equation

HRID 1463316 reaction equation
[CH2:1]([S:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)(=[O:5])=[O:4])[CH3:2].[C:16]([OH:20])(=[O:19])[CH:17]=[CH2:18].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH2:1]([S:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH2:18][CH2:17][C:16]([OH:20])=[O:19])(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 7918Acetic AnhydrideHCID 22611238HCID 22611238, compound

Product 1

HCID 19921623HCID 19921623, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-ethanesulfonylamino-1H-indole (8.0 g, 36 mmol), acrylic acid (5.15 g, 71 mmol), and acetic anhydride (7.3 g, 71 mmol) in 35 mL of acetic acid was heated at 90° C. for 20 h. The volatile materials were removed under high vacuum at 90° C. The remaining residue was dissolved in 1N NaOH and subsequently acidified to pH 1 with concentrated HCl. The aqueous solution was then extracted with five portions of ethyl acetate. The organic extracts were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to yield 3-(5-ethanesulfonylamino-1H-indol-3-yl)propanoic acid (10.6 g of crude material). NMR and mass spectral analysis indicated the presence of the desired product. No attempt was made to purify this material; it was immediately subjected to reduction as described below.

Workup

  1. customThe volatile materials were removed under high vacuum at 90° C
  2. dissolutionThe remaining residue was dissolved in 1N NaOH
  3. extractionThe aqueous solution was then extracted with five portions of ethyl acetate
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bd44a6778584eda83c4f881c018675f
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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