Water → 1-Acetyl-3-(4-tert-butyldiphenylsilyloxymethyl-3-methylphenyl)methylene-2,5-piperazinedione

HRID 584214Notes

Reaction equation

HRID 584214 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[CH3:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([N:32]1[CH2:37][C:36](=[O:38])[N:35](C(=O)C)[CH2:34][C:33]1=[O:42])(=[O:31])[CH3:30].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(C)(C)C>[C:29]([N:32]1[CH2:37][C:36](=[O:38])[NH:35][C:34](=[CH:24][C:23]2[CH:26]=[CH:27][C:20]([CH2:19][O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:21]([CH3:28])[CH:22]=2)[C:33]1=[O:42])(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 5403711,4-Diacetyl-2,5-piperazinedioneHCID 223429234-(Tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 696776911-Acetyl-3-(4-tert-butyldiphenylsilyloxymethyl-3-methylphenyl)methylene-2,5-piperazinedioneYield 71.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred mixture of 4-(tert-butyldiphenylsilyloxymethyl)-3-methylbenzaldehyde (1.94 g) and 1,4-diacetyl-2,5-piperazinedione (991 mg) in a mixture of N,N-dimethylformamide (10 ml) and tert-butanol (10 ml) was added potassium tert-butoxide (561 mg) at 5° C. The mixture was stirred for 1 hour at room temperature and then poured into water (300 ml), and stirring was continued for 18 hours at room temperature. The resulting precipitates were collected by filtration and washed with water and isopropyl ether, and dried under reduced pressure to give 1-acetyl-3-(4-tert-butyldiphenylsilyloxymethyl-3-methylphenyl)methylene-2,5-piperazinedione (1.88 g) as a powder.

Workup

  1. stirringstirring
  2. waitwas continued for 18 hours at room temperature
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water and isopropyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-de72eff2dc114209b7ca7de62477dd76
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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