Sodium Hydroxide → HCID 66680556, compound

HRID 1966965Notes

Reaction equation

HRID 1966965 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:12](=[O:13])[C:11]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:10]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:9]1=[O:26])C>C1COCC1>[O:26]=[C:9]1[N:8]([CH2:7][C:6]([OH:27])=[O:5])[C:12](=[O:13])[C:11]2([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[N:10]1[C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66679752HCID 66679752, compound

Product 1

HCID 66680556HCID 66680556, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

172 ml (0.172 mol; 1.5 eq.) of 1N sodium hydroxide are added to a solution of 39.5 g (0.114 mol; 1 eq.) of (2,4-dioxo-1-p-tolyl-1,3-diazaspiro[4.5]dec-3-yl)acetic acid ethyl ester in 400 ml of THF. The reaction medium is stirred at room temperature for about 72 hours. The reaction medium is concentrated and 250 ml of ethyl acetate are added, followed by 400 ml of water. 100 ml of 1N NaOH are added and the aqueous solution is washed with 250 ml of ethyl acetate. The aqueous phase is concentrated and then acidified to pH 4 approximately with 170 ml of 1N acetic acid. The white precipitate is filtered off and then rinsed with water until the pH of the filtrates is approximately equal to 7, and dried in an oven under vacuum at 40° C. The product (2,4-dioxo-1-p-tolyl-1,3-diazaspiro[4.5]dec-3-yl)acetic acid is obtained in the form of a white solid.

Workup

  1. concentrationThe reaction medium is concentrated
  2. addition250 ml of ethyl acetate are added
  3. addition100 ml of 1N NaOH are added
  4. washthe aqueous solution is washed with 250 ml of ethyl acetate
  5. concentrationThe aqueous phase is concentrated
  6. filtrationThe white precipitate is filtered off
  7. washrinsed with water until the pH of the filtrates
  8. customdried in an oven under vacuum at 40° C

Sources & evidence

ORD record
ord-32559c43b1d041f9baa72d9c71be477a
Source dataset
uspto-grants-2013_04
Patent number
US08420681B2

Reaction notes

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