Lithium Hydroxide → HCID 68358320, compound

HRID 588990Notes

Reaction equation

HRID 588990 reaction equation
[CH3:1][N:2]1[C@@:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:15]([O:17]C)=[O:16])[CH:12]=3)[CH2:7]2)[C:5](=[O:19])[NH:4][C:3]1=[O:20].[OH-].[Li+]>C1COCC1.O>[CH3:1][N:2]1[C@@:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=3)[CH2:7]2)[C:5](=[O:19])[NH:4][C:3]1=[O:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86707238HCID 86707238, compound

Product 1

HCID 68358320HCID 68358320, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl (4S)-3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidine-4,2′-indene]-5′-carboxylate (1.40 g, 5.10 mmol) in THF (30 mL) and H2O (15 mL) was added 1.0 N aqueous lithium hydroxide (20.4 mL, 20.4 mmol) and the reaction mixture was stirred at ambient temperature for 18 h. The THF was removed in vacuo and the resulting mixture was adjusted to pH=1 by addition of 1.0 N HCl. The precipitate was isolated by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=260.9 (M+1); 1H NMR (400 MHz, DMSO-d6) δ 12.85 (br s, 1H), 10.98 (br s, 1H), 7.82 (s, 1H), 7.81 (d, 1H, J=8.4 Hz), 7.37 (d, 1H, J=8.4 Hz), 3.38-3.28 (m, 4H), 2.56 (2, 3H).

Workup

  1. customThe THF was removed in vacuo
  2. additionthe resulting mixture was adjusted to pH=1 by addition of 1.0 N HCl
  3. customThe precipitate was isolated by filtration
  4. washwashed with H2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dac0d8e66ad845fabaee8f79aaf7ffb7
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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