Lithium hydroxide, monohydrate → HCID 10299128, compound

HRID 428692Notes

Reaction equation

HRID 428692 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:33])[C:13]#[C:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2/[C:17](=[CH:25]/[C:26]2[NH:27][CH:28]=[CH:29][C:30]=2[O:31][CH3:32])/[C:18](=[O:24])[NH:19]3)=[CH:8][C:7]=1[O:34][CH3:35].O[Li].O>C1COCC1.O>[CH3:32][O:31][C:30]1[CH:29]=[CH:28][NH:27][C:26]=1/[CH:25]=[C:17]1\[C:18](=[O:24])[NH:19][C:20]2[C:16]\1=[C:15]([C:14]#[C:13][CH:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([O:34][CH3:35])[CH:8]=1)[OH:33])[CH:23]=[CH:22][CH:21]=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10163302HCID 10163302, compound

Product 1

HCID 10299128HCID 10299128, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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]-2-methoxyphenoxy]acetic acid methyl ester(28 mg, 0.057 mmol) (from Example 47) was hydrolyzed with LiOH.H2O (55 mg, 1.15 mmol) in THF (0.5 mL) and H2O (0.5 mL) at room temperature for 20 h according to Method F above 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]-2-methoxyphenoxy]acetic acid. (Yield 22 mg, 81%).

Sources & evidence

ORD record
ord-38eb621fde644b8ba1122e4e87d0ade4
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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