Methanol → HCID 14746212, compound

HRID 375770Notes

Reaction equation

HRID 375770 reaction equation
[CH2:1]([N:3]([C:14]1[N:19]=[C:18]([N:20]([CH:23]2[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]2)[CH2:21][CH3:22])[N:17]=[C:16]([O:33][CH2:34][CH2:35][OH:36])[N:15]=1)[CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[NH:7][C:6]([CH3:13])([CH3:12])[CH2:5]1)[CH3:2].[C:37]([O:45][CH3:46])(=[O:44])[CH2:38][CH2:39][C:40]([O:42]C)=O.[CH3:47][OH:48]>C1(C)C=CC=CC=1.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH2:21]([N:20]([C:18]1[N:19]=[C:14]([N:3]([CH:4]2[CH2:9][C:8]([CH3:10])([CH3:11])[NH:7][C:6]([CH3:13])([CH3:12])[CH2:5]2)[CH2:1][CH3:2])[N:15]=[C:16]([O:33][CH2:34][CH2:35][O:36][C:40](=[O:42])[CH2:39][CH2:38][C:37]([O:45][CH2:46][CH2:47][O:48][C:16]2[N:17]=[C:18]([N:20]([CH2:21][CH3:22])[CH:23]3[CH2:28][C:27]([CH3:29])([CH3:30])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]3)[N:19]=[C:14]([N:3]([CH:4]3[CH2:5][C:6]([CH3:13])([CH3:12])[NH:7][C:8]([CH3:10])([CH3:11])[CH2:9]3)[CH2:1][CH3:2])[N:15]=2)=[O:44])[N:17]=1)[CH:23]1[CH2:24][C:25]([CH3:32])([CH3:31])[NH:26][C:27]([CH3:30])([CH3:29])[CH2:28]1)[CH3:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 7820Dimethyl SuccinateHCID 14746200HCID 14746200, compound

Product 1

HCID 14746212HCID 14746212, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Procedure

1.60 g of 2,4-bis-[N-ethyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]-6-(2-hydroxyethoxy)-1,3,5-triazine [prepared as described in Preparation 3(B)] and 0.22 g of dimethyl succinate were dissolved in 20 ml of toluene, and a catalytic amount of tetraisopropyl titanate was added to the resulting solution. The resulting mixture was first agitated at 100° to 105° C. for 3 hours whilst the methanol generated was removed by distillation, and then the temperature was elevated to 130° C. to remove the toluene. When this removal was complete, a mixture of ethyl acetate and water was added to the residue, and then the mixture was shaken. The ethyl acetate layer was then separated, dried and concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (using a 10:3:1 by volume mixture of diethyl ether, ethanol and triethylamine as eluent), to obtain 920 mg of the title compound as crystals melting at 85° C.

Workup

  1. customgenerated was removed by distillation
  2. customwas elevated to 130° C.
  3. customto remove the toluene
  4. customWhen this removal
  5. additiona mixture of ethyl acetate and water
  6. additionwas added to the residue
  7. customThe ethyl acetate layer was then separated
  8. customdried
  9. concentrationconcentrated by evaporation under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (
  11. additionby volume mixture of diethyl ether, ethanol and triethylamine as eluent),

Sources & evidence

ORD record
ord-da7a5e3f69df4c10ad5757b1aeb61796
Source dataset
uspto-grants-1996_01
Patent number
US05486556

Reaction notes

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