2,2-Bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane → 2,2-Bis{4-[2-acetoxy-3-(8-acetyl-7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

HRID 972025Notes

Reaction equation

HRID 972025 reaction equation
[OH:1][CH:2]([CH2:41][N:42]1[C:46](=[O:47])[C:45]2([CH2:52][C:51]([CH3:54])([CH3:53])[NH:50][C:49]([CH3:56])([CH3:55])[CH2:48]2)[NH:44][C:43]1=[O:57])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([OH:40])[CH2:23][N:24]3[C:28](=[O:29])[C:27]4([CH2:34][C:33]([CH3:36])([CH3:35])[NH:32][C:31]([CH3:38])([CH3:37])[CH2:30]4)[NH:26][C:25]3=[O:39])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1>C(OC(=O)C)(=O)C>[C:17]([O:40][CH:22]([CH2:23][N:24]1[C:28](=[O:29])[C:27]2([CH2:34][C:33]([CH3:35])([CH3:36])[N:32]([C:2](=[O:1])[CH3:3])[C:31]([CH3:37])([CH3:38])[CH2:30]2)[NH:26][C:25]1=[O:39])[CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([O:1][C:5](=[O:4])[CH3:6])[CH2:41][N:42]3[C:46](=[O:47])[C:45]4([CH2:48][C:49]([CH3:56])([CH3:55])[N:50]([C:28](=[O:29])[CH3:27])[C:51]([CH3:54])([CH3:53])[CH2:52]4)[NH:44][C:43]3=[O:57])=[CH:10][CH:9]=2)([CH3:13])[CH3:12])=[CH:15][CH:16]=1)(=[O:20])[CH3:16]

Participants

3

Reactant 1

HCID 234627182,2-Bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

Product 1

HCID 203967992,2-Bis{4-[2-acetoxy-3-(8-acetyl-7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

5 g of 2,2-bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane were heated at 100°-110° C. in 100 ml of acetic anhydride, with stirring, for 6 hours. After completion of the reaction, the reaction mixture was condensed by evaporation under reduced pressure and then 150 ml of benzene were added to dissolve the residue. The benzene solution was washed successively with a 2% w/w sodium carbonate solution and water. The solvent was then removed and the residue was purified by column chromatography through silica gel eluted with a 8:1:1:1 by volume mixture of ethyl acetate, benzene, ethanol, and triethylamine. The desired Compound No. 68 was obtained in the form of white crystals, melting point 147°-149° C.

Workup

  1. customAfter completion of the reaction
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. addition150 ml of benzene were added
  5. dissolutionto dissolve the residue
  6. washThe benzene solution was washed successively with a 2% w/w sodium carbonate solution and water
  7. customThe solvent was then removed
  8. customthe residue was purified by column chromatography through silica gel
  9. washeluted with a 8:1:1:1 by volume mixture of ethyl acetate, benzene, ethanol, and triethylamine
  10. custom68 was obtained in the form of white crystals, melting point 147°-149° C.

Sources & evidence

ORD record
ord-f0547bc6cba74bea973bcce9b774d0c9
Source dataset
uspto-grants-1979_07
Patent number
US04162246

Reaction notes

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