Water → HCID 22678035, compound

HRID 1837535Notes

Reaction equation

HRID 1837535 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][C:15]2([S:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[S:19][C:18](=[O:20])[NH:17][C:16]2=[O:21])=[C:6]([CH3:33])[CH:5]=1.[OH-].[Li+].O>C1COCC1.CO>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([S:22]([C:15]2([CH2:14][CH2:13][CH2:12][C:11]#[C:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:34])=[O:2])=[CH:5][C:6]=3[CH3:33])[S:19][C:18](=[O:20])[NH:17][C:16]2=[O:21])(=[O:23])=[O:24])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 10164021HCID 10164021, compound

Product 1

HCID 22678035HCID 22678035, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{5-[5-(4-methoxybenzenesulfonyl)-2,4-dioxo-thiazolidin-5-yl]pent-1-ynyl}-3-methylbenzoic acid methyl ester (Example 160)(0.29 g, 0.536 mmol) in THF (30 ml plus sufficient methanol to dissolve the substrate) was added lithium hydroxide (0.75 ml of 1.0M in water), and this solution was stirred at room temperature for 3 days. Dilution with water and acidification gave a solid which was crystallized from hexane-ethyl acetate to give the title compound as a light yellow solid mp 182-184° C. THEORY: C, 56.66, H, 4.34, N, 2.87. FOUND: C, 56.39, H, 4.60, N, 2.80.

Workup

  1. customwas crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-8e19b327946e4a30bd3a4da7546557d8
Source dataset
uspto-grants-2004_08
Patent number
US06784184B2

Reaction notes

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