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Water → 3-(2,5-Dimethyl-phenyl)-4-ethoxymethoxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one

HRID 1962379
Notes
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Reaction equation

HRID 1962379 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[C:10](=[O:22])[NH:11][C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:13]=1[OH:14].CCN(C(C)C)C(C)C.[CH2:32]([O:34][CH2:35]Cl)[CH3:33].O>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[C:10](=[O:22])[NH:11][C:12]2([CH2:19][CH2:18][N:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[C:13]=1[O:14][CH2:35][O:34][CH2:32][CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 18523Chloromethyl ethyl etherHCID 81531DiisopropylethylamineHCID 547422463-(2,5-Dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one2×

Product 1

HCID 580312593-(2,5-Dimethyl-phenyl)-4-ethoxymethoxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To 250 mg of 3-(2,5-dimethyl-phenyl)-4-hydroxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (compound C1, preparation example P1, step P1.5) in 2.5 ml of tetrahydrofuran were added 160 μl of Hünig's base and 85 μl of chloromethyl ethyl ether. After stirring for 20 hours at room temperature, water and ethyl acetate were added and the layers were separated. The aqueous phase was extracted with ethyl acetate, the combined organic phases dried with sodium sulfate, filtered and concentrated. Chromatography (heptane/acetone 4:1) yielded 72 mg of 3-(2,5-dimethyl-phenyl)-4-ethoxymethoxy-8-methoxy-1,8-diaza-spiro[4.5]dec-3-en-2-one (title compound A61) as a solid, mp: 150-152° C.

Workup

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

Sources & evidence

ORD record
ord-29b2fb4fdd0d4a4d93fd252c566109f9
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415369B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes