Lithium hydroxide, monohydrate → HCID 10180013, compound

HRID 428659Notes

Reaction equation

HRID 428659 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:31])[C:11]#[C:12][C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2/[C:15](=[CH:23]/[C:24]2[NH:25][CH:26]=[CH:27][C:28]=2[O:29][CH3:30])/[C:16](=[O:22])[NH:17]3)=[CH:6][CH:5]=1.O[Li].O>C1COCC1.O>[CH3:30][O:29][C:28]1[CH:27]=[CH:26][NH:25][C:24]=1/[CH:23]=[C:15]1\[C:16](=[O:22])[NH:17][C:18]2[C:14]\1=[C:13]([C:12]#[C:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=1)[OH:31])[CH:21]=[CH:20][CH:19]=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 9932323HCID 9932323, compound

Product 1

HCID 10180013HCID 10180013, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using Method F above, 4-[1-hydroxy-3-[3-(3-methoxy-1H-pyrrol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-4-yl]-prop-2-ynyl]-benzoic acid methyl ester (30 mg, 0.07 mmol) (from Example 12 above) was hydrolyzed with LiOH.H2O (13 mg, 2.7 mmol) in THF (1 mL) and water (1 mL) at room temperature for 18 h, to yield rac-(Z)-4-[3-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-1-hydroxy-2-propynyl]benzoic acid. (Yield 21 mg, 72%).

Sources & evidence

ORD record
ord-1bffa6b8917f4fd18d5376a4b6e8a5ad
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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