Lithium hydroxide, monohydrate → HCID 10114392, compound

HRID 428698Notes

Reaction equation

HRID 428698 reaction equation
CC([O:5][C:6](=[O:37])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:36])[C:16]#[C:17][C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2/[C:20](=[CH:28]/[C:29]2[NH:30][CH:31]=[CH:32][C:33]=2[O:34][CH3:35])/[C:21](=[O:27])[NH:22]3)=[CH:11][CH:10]=1)(C)C.O[Li].O>C1COCC1.O>[CH3:35][O:34][C:33]1[CH:32]=[CH:31][NH:30][C:29]=1/[CH:28]=[C:20]1\[C:21](=[O:27])[NH:22][C:23]2[C:19]\1=[C:18]([C:17]#[C:16][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]([OH:37])=[O:5])=[CH:14][CH:13]=1)[OH:36])[CH:26]=[CH:25][CH:24]=2

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10163961HCID 10163961, compound

Product 1

HCID 10114392HCID 10114392, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using Method F above, 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]phenoxy]acetic acid 1,1-dimethylethyl ester (from Example 58 above) (30 mg, 0.061 mmol) was hydrolyzed with LiOH.H2O (58 mg, 1.22 mmol) in THF (0.5 mL) and H2O (0.5 mL) for 12 h, yielding 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]phenoxy]acetic acid. (Yield 24 mg, 89%).

Sources & evidence

ORD record
ord-f5916fa34c2f49889852ff8b5af83b8e
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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