Glycolic Acid → 3-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid carboxymethyl ester

HRID 1827003Notes

Reaction equation

HRID 1827003 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:25])[N:11]([C:18](N2C=CN=C2)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:26]([OH:30])(=[O:29])[CH2:27][OH:28].C(O)(C(F)(F)F)=O>C1COCC1.C(OCC)(=O)C.O>[C:26]([CH2:27][O:28][C:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:9](=[CH:8]/[C:3]2[NH:4][C:5]([CH3:7])=[CH:6][C:2]=2[CH3:1])/[C:10]1=[O:25])=[O:19])([OH:30])=[O:29]

Participants

7

Reactant 3

HCID 757Glycolic AcidHCID 6422Trifluoroacetic acidHCID 601112313-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one

Product 1

HCID 601112393-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid carboxymethyl esterYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture of 3-[1-(3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indole-2-one (166 mg, 0.5 mmol), glycolic acid (163 mg, 1.5 mmol, 70% w/w in water) and (68 mg, 0.6 mmol) of TFA in 3 mL of THF was stirred at room temperature for 4 h and diluted with ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The precipitate was filtered, washed with small amount of ethyl acetate, and dried in a vacuum oven overnight to afford 42 mg (25%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid carboxymethyl ester. 1H NMR (400 MHz, DMSO-d6 and CDCl3) δ 12.63 (s, 1H, NH-1′), 7.92–7.94 (m, 1H), 7.52–7.55 (m, 1H), 7.44 (s, 1H, H-vinyl), 7.20–7.22 (m, 2H), 6.06 (s, br, 1H, H-4′), 4.94 (s, 2H, CH2), 2.39 (s, 3H, CH3), and 2.36 (s, 3H, CH3).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. filtrationThe precipitate was filtered
  5. washwashed with small amount of ethyl acetate
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-235154e501144574afa6b47d686e565a
Source dataset
uspto-grants-2006_05
Patent number
US07053114B2

Reaction notes

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