Hydrochloric Acid → HCID 131719389, compound

HRID 1721548Notes

Reaction equation

HRID 1721548 reaction equation
CC(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([NH2:17])[C:14]([OH:16])=[O:15])=O)(C)C.[C:18]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.[C:36](Cl)(=[O:39])[CH:37]=[CH2:38].C([O-])(=O)C=C.OCCOC(=O)C(C)=C>C(OCC)(=O)C.C(O)C.C(=O)(O)[O-].N(C(C)(C)C#N)=NC(C)(C)C#N>[C:18]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:17][C@H:13]([C:14]([O:16][C:36](=[O:39])[CH:37]=[CH2:38])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][NH2:8])=[O:31])=[CH:28][CH:27]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

11

Reactant 6

HCID 313Hydrochloric AcidHCID 13140Acryloyl chlorideHCID 133602-Hydroxyethyl MethacrylateHCID 25188AcrylateHCID 544580Lysine, N6-[(1,1-dimethylethoxy)carbonyl]-HCID 129121414-Benzoylbenzoyl chloride

Product 1

HCID 131719389HCID 131719389, compound

Reagents, catalysts & solvents 4

HCID 6547AzobisisobutyronitrileCatalystHCID 702EthanolSolventHCID 769Bicarbonate IonSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Benzoylbenzoyl-lysyl-acrylate (BBA-LYS-AC) is prepared by reacting N-epsilon-t-BOC-L-lysine with 4-benzoylbenzoyl chloride, then deblocking the epsilon-amino group with 3N HCl in ethyl acetate for one hour at room temperature followed by reaction with acryloyl chloride at pH 9.0. This reagent is coated onto silicone contact lenses by incubating the reagent solution in 50% ethanol in 0.1M bicarbonate buffer at pH 9.5 for two hours at room temperature, then exposing to high intensity light at 305 nm. The acrylate is the polymerization site. A solution of 5% hydroxyethylmethacrylate in 0.1M bicarbonate buffer at pH 9.0 is then polymerized on the lenses using 2,2'-azobisisobutyronitrile as catalyst. The polymerization reaction is allowed to proceed for one hour at room temperature, after which the uncoupled polymer is removed by washing the plates. This procedure improves wettability of the lenses.

Workup

  1. customfor one hour
  2. customat room temperature
  3. customfor two hours
  4. customat room temperature
  5. customThe polymerization reaction
  6. customafter which the uncoupled polymer is removed
  7. washby washing the plates

Sources & evidence

ORD record
ord-1190880cae1a4817a969c90c3452a429
Source dataset
uspto-grants-1996_04
Patent number
US05512329

Reaction notes

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