Triethylamine → HCID 88243341, compound

HRID 377532Notes

Reaction equation

HRID 377532 reaction equation
C(N(CC)CC)C.Cl[CH:9]([O:11][CH2:12][CH2:13][O:14]CCOC(Cl)C)[CH3:10].C(OC([O-])=O)(OC(C)(C)C)=[O:22].[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33]>CN(C)C=O.O>[OH:34][CH:32]([O:35][CH2:36][CH2:37][O:14][CH2:13][CH2:12][O:11][CH:9]([OH:22])[CH3:10])[CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 18786803HCID 18786803, compoundHCID 22064466Tert-butyldicarbonate

Product 1

HCID 88243341HCID 88243341, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g, was dissolved in 180 g of N,N-dimethylformamide. With stirring under ice cooling, 30.0 g of triethylamine and then 2.0 g of diethylene glycol di(1-chloroethyl) ether were added. Reaction was carried out for 30 minutes under ice cooling, 35.0 g of tert-butyl dicarbonate was added, and reaction was carried out for a further 2 hours at 40° C. After the reaction mixture was allowed to cool down to room temperature, 500 g of ethyl acetate and 300 g of water were added thereto, followed by separation. The ethyl acetate layer was washed twice with 300 g of water and then concentrated in vacuum. The residue was dissolved in 300 g of methanol and added dropwise to 20 liters of water whereupon a powdery solid precipitated. The solid was collected by filtration, washed with 20 liters of water, and dried in vacuum at 40° C. for 24 hours. On 1H-NMR analysis, it was identified to be a polymer (Polym. 6) in which 18.0 mol % of the hydrogen atoms of hydroxyl groups in polyhydroxystyrene were replaced by tert-butoxycarbonyl groups, and the carboxyl group moieties which had been introduced in an amount of 2.0 mol % formed ester bonds with alcoholic hydroxyl groups of diethylene glycol di(1-hydroxyethyl) ether to provide crosslinking.

Workup

  1. customThe thus obtained partially hydroxycarbonylmethylated polyhydroxystyrene, 90 g
  2. customReaction
  3. customreaction
  4. waitwas carried out for a further 2 hours at 40° C
  5. customfollowed by separation
  6. washThe ethyl acetate layer was washed twice with 300 g of water
  7. concentrationconcentrated in vacuum
  8. dissolutionThe residue was dissolved in 300 g of methanol
  9. additionadded dropwise to 20 liters of water whereupon a powdery solid
  10. customprecipitated
  11. filtrationThe solid was collected by filtration
  12. washwashed with 20 liters of water
  13. customdried in vacuum at 40° C. for 24 hours
  14. additionthe carboxyl group moieties which had been introduced in an amount of 2.0 mol %

Sources & evidence

ORD record
ord-276d96f67c8d4a27b540c5876c32af96
Source dataset
uspto-grants-2000_02
Patent number
US06027854

Reaction notes

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