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 1008117Notes

Reaction equation

HRID 1008117 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-7a9e387b26254a40a7d38ce38e01aa46
Source dataset
uspto-grants-2004_09
Patent number
US06797725B2

Reaction notes

Loading…