Sodium Hydroxide → 4-(4-(7-(4-Cyano-3-(trifluoromethyl)phenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)phenyl)butanoic acid

HRID 1192861Notes

Reaction equation

HRID 1192861 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:20](=[S:21])[N:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=3)[C:18](=[O:34])[C:14]32[CH2:17][CH2:16][CH2:15]3)=[CH:9][CH:8]=1.[OH-].[Na+]>CO>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([N:19]2[C:18](=[O:34])[C:14]3([CH2:15][CH2:16][CH2:17]3)[N:13]([C:10]3[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[CH:12][CH:11]=3)[C:20]2=[S:21])=[CH:23][C:24]=1[C:30]([F:31])([F:32])[F:33])#[N:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866300064-{4-[7-(4-Cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}-butyric acid methyl ester

Product 1

HCID 866098664-(4-(7-(4-Cyano-3-(trifluoromethyl)phenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)phenyl)butanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-{4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-phenyl}-butyric acid methyl ester (90) [ND-4] (0.501 g, 1 mmol) in methanol (10 ml) and solution of sodium hydroxide (10 ml, 2M) was stirred at room temperature for 5 hours. The methanol was evaporated. The residue was adjusted to pH=5 by HCl aq. (2M) and then, the medium was extracted with ethyl acetate (3×50 ml). The organic layer was dried over MgSO4 and concentrated to dryness to obtain 4-{4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]-phenyl}-butyric acid (89) [ND-5] (0.482 g, 0.99 mmol, 99%), the structure of which is illustrated in Formula 89.

Workup

  1. customThe methanol was evaporated
  2. extractionthe medium was extracted with ethyl acetate (3×50 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5b3a59c98b49430e98108524eb2a4cc0
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

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