Tetraethoxysilane → 3-[8-(3,5-Bis-trifluoromethyl-benzoyl)-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-yl]-propionic acid ethyl ester

HRID 1018568Notes

Reaction equation

HRID 1018568 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:24][CH2:23][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][NH:13][C:12]2=[O:22])[CH2:10][CH2:9]1)=[O:7].[F-].[Cs+].C(O[Si](OCC)(OCC)OCC)C.[C:49]([O:53][CH2:54][CH3:55])(=[O:52])[CH:50]=[CH2:51]>C1COCC1>[CH2:54]([O:53][C:49](=[O:52])[CH2:50][CH2:51][N:13]1[C:12](=[O:22])[C:11]2([CH2:10][CH2:9][N:8]([C:6](=[O:7])[C:5]3[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:4]=3)[CH2:24][CH2:23]2)[N:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14]1)[CH3:55]

Participants

6

Reactant 4

HCID 6517TetraethoxysilaneHCID 8821Ethyl AcrylateHCID 25953Cesium fluorideHCID 184017258-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

Product 1

HCID 865841833-[8-(3,5-Bis-trifluoromethyl-benzoyl)-4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]dec-3-yl]-propionic acid ethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 8-(3,5-bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (1.0 g, 2.1 mmol), cesium fluoride (32 mg, 0.21 mmol) and tetraethoxysilane (475 μL, 2.1 mmol) in THF (10 mL) was added ethyl acrylate (254 μL, 2.3 mmol). The mixture was stirred for 1 d at room temperature. Evaporation of the solvent yielded a residue which was purified by chromatography on silica gel (ethyl acetate/n-hexane 1:2) to yield the desired product (0.9 g, 75%), MS: m/e=572.1 (M+H+).

Workup

  1. customEvaporation of the solvent
  2. customyielded a residue which
  3. customwas purified by chromatography on silica gel (ethyl acetate/n-hexane 1:2)

Sources & evidence

ORD record
ord-5de6f65f4fec4f2eb3106948054e167b
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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