Water → 2,2-Dimethyl-propionic acid 8-ethoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester

HRID 1022378

Reaction equation

HRID 1022378 reaction equation
[CH2:1]([O:3][N:4]1[CH2:24][CH2:23][C:7]2([NH:11][C:10](=[O:12])[C:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:8]2[OH:22])[CH2:6][CH2:5]1)[CH3:2].N1C=CC=CC=1.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].O>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][N:4]1[CH2:5][CH2:6][C:7]2([NH:11][C:10](=[O:12])[C:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:8]2[O:22][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:23][CH2:24]1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 596145818-Ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one

Product 1

HCID 580312652,2-Dimethyl-propionic acid 8-ethoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 143 mg of 8-ethoxy-4-hydroxy-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-2-one in 1 ml of tetrahydrofuran are added 36 □l of pyridine and 53 □l of pivaloyl chloride. After stirring at room temperature for 20 hours, water and ethyl acetate are added and the phases separated. The aqueous phase is extracted with ethyl acetate, the combined organic phases dried with sodium sulfate, filtered and concentrated. Chromatography (heptane/ethyl acetate 2:1) yielded 117 mg of 2,2-dimethyl-propionic acid 8-ethoxy-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester as a solid, mp: 230-231° C.

Workup

  1. customthe phases separated
  2. extractionThe aqueous phase is extracted with ethyl acetate
  3. dry with materialthe combined organic phases dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a2d992888f647fb973876ca75fa9234
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Linked notes

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