Acetic Anhydride → HCID 20396811, compound

HRID 972027Notes

Reaction equation

HRID 972027 reaction equation
[OH:1][CH:2]([CH2:44][N:45]1[C:49](=[O:50])[C:48]2([CH2:55][C:54]([CH3:57])([CH3:56])[N:53]([CH2:58][CH2:59][OH:60])[C:52]([CH3:62])([CH3:61])[CH2:51]2)[NH:47][C:46]1=[O:63])[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:43])[CH2:23][N:24]3[C:28](=[O:29])[C:27]4([CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([CH2:37][CH2:38][OH:39])[C:31]([CH3:41])([CH3:40])[CH2:30]4)[NH:26][C:25]3=[O:42])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1.C(O[C:68](=[O:70])[CH3:69])(=O)C>>[C:17]([O:1][CH:2]([CH2:44][N:45]1[C:49](=[O:50])[C:48]2([CH2:51][C:52]([CH3:62])([CH3:61])[N:53]([CH2:58][CH2:59][O:60][C:2](=[O:1])[CH3:3])[C:54]([CH3:57])([CH3:56])[CH2:55]2)[N:47]([C:68](=[O:70])[CH3:69])[C:46]1=[O:63])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([O:43][C:5](=[O:4])[CH3:6])[CH2:23][N:24]3[C:28](=[O:29])[C:27]4([CH2:30][C:31]([CH3:40])([CH3:41])[N:32]([CH2:37][CH2:38][O:39][C:38](=[O:39])[CH3:37])[C:33]([CH3:35])([CH3:36])[CH2:34]4)[N:26]([C:28](=[O:29])[CH3:27])[C:25]3=[O:42])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:9][CH:10]=1)(=[O:20])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 20396807HCID 20396807, compound

Product 1

HCID 20396811HCID 20396811, compound

Procedure

A mixture of 1 g of 2,2-bis{4-[2-hydroxy-3-(8-β-hydroxyethyl-7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane (obtained as described in Example 18) and 20 g of acetic anhydride was refluxed for 60 hours. After completion of the reaction, the reaction mixture was poured into ammoniacal ice-water, extracted with benzene and then purified by column chromatography through silica gel eluted with a 2:1 by volume mixture of benzene and ethyl acetate, to give the desired Compound No. 188 in the form of white crystals. The compound had an Rf value of 0.86 on thin-layer chromatography on silica gel using a 1:1:1 by volume mixture of n-hexane, benzene and ethyl acetate as developing solvent.

Workup

  1. temperaturewas refluxed for 60 hours
  2. customAfter completion of the reaction
  3. extractionextracted with benzene
  4. custompurified by column chromatography through silica gel
  5. washeluted with a 2:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-812504aeb8bb468a9fe60a4367e70547
Source dataset
uspto-grants-1979_07
Patent number
US04162246

Reaction notes

Loading…