Sodium Hydroxide → HCID 86609858, compound

HRID 245007Notes

Reaction equation

HRID 245007 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:18](=[S:19])[N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=3)[C:16](=[O:32])[C:12]32[CH2:15][CH2:14][CH2:13]3)=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([N:17]2[C:16](=[O:32])[C:12]3([CH2:13][CH2:14][CH2:15]3)[N:11]([C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:33])=[O:2])=[CH:10][CH:9]=3)[C:18]2=[S:19])=[CH:21][C:22]=1[C:28]([F:30])([F:31])[F:29])#[N:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86609857HCID 86609857, compound

Product 1

HCID 86609858HCID 86609858, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of {4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]phenyl}acetic acid methyl ester (46b) (0.095 g, 0.2 mmol) and a solution of sodium hydroxide (1 ml, 2M) in methanol (2 ml) was stirred at room temperature for 2 hours. The methanol was evaporated. The residue was adjusted to pH 5 by aq. 2M HCl and then the mixture was extracted with ethyl acetate (3×10 ml). The organic layer was dried over MgSO4 and concentrated to dryness to obtain {4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]phenyl}acetic acid (46c) [RD147] (0.087 g, 0.19 mmol, 95%), the structure of which is illustrated in Formula 16.

Workup

  1. customThe methanol was evaporated
  2. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f78470989e134d6d9a532960ea2178c3
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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