Lithium hydroxide, monohydrate → (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid

HRID 382069Notes

Reaction equation

HRID 382069 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]([NH:19][C:20](=[O:27])[CH2:21][C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][CH:16]=[C:15]3[C:11]=2/[C:12](=[CH:29]/[C:30]2[NH:31][CH:32]=[CH:33][C:34]=2[O:35][CH3:36])/[C:13](=[O:28])[NH:14]3)=[CH:6][CH:5]=1.O[Li].O>C1COCC1.O>[CH3:36][O:35][C:34]1[CH:33]=[CH:32][NH:31][C:30]=1/[CH:29]=[C:12]1\[C:13](=[O:28])[NH:14][C:15]2[C:11]\1=[C:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=1)[C:18]([NH:19][C:20](=[O:27])[CH2:21][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[CH:17][CH:16]=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 9871087(Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid methyl ester

Product 1

HCID 9805948(Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acidYield 29%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using Method F above, (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid methyl ester (70 mg, 0.14 mmol) (from Example 50 supra) was hydrolyzed with LiOH.H2O (20 mg, 0.48 mmol) in THF (3 mL) and water (2 mL) at room temperature for 3 days to yield (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid (yield: 20 mg, 29%).

Sources & evidence

ORD record
ord-76834a2ec4ff47bea60d9694c29243f5
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

Loading…