N6-(2,4-Dinitrophenyl)-L-lysine → HCID 44593781, compound

HRID 964768Notes

Reaction equation

HRID 964768 reaction equation
[NH2:1][C@H:2]([C:20]([OH:22])=[O:21])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:19]=[CH:18][C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:9]=1[N+:10]([O-:12])=[O:11].C1C(=O)N([O:30][C:31]([O:33][CH2:34][CH:35]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41]3[C:36]2=[CH:37][CH:38]=[CH:39][CH:40]=3)=O)C(=O)C1>C(COC)OC.C([O-])([O-])=O.[Na+].[Na+]>[NH:1]([C:31]([O:33][CH2:34][CH:35]1[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:42]2[C:47]1=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:30])[C@H:2]([C:20]([OH:22])=[O:21])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[CH:19]=[CH:18][C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 65068N6-(2,4-Dinitrophenyl)-L-lysine2×HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Product 1

HCID 44593781HCID 44593781, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

Fmoc-Lys(Dnp) was prepared from Lys(Dnp) as follows. Fmoc N-hydroxysuccinimide ester (1.89 g; 5.60 mmol) was dissolved in 30 mL of dimethoxyethane and stored at 4° C. Lys(Dnp) (1.63 g; 4.67 mmol) was dissolved in 10 mL of 10% aqueous Na2CO3 and added slowly to the dimethoxyethane solution. The reaction proceeded for 2 hours at 4° C. and overnight at room temperature. The solution was filtered, and the filtrate acidified to a pH of about 3 with concentrated HCl. Dimethoxyethane was removed by heating the solution under reduced pressure. The solution was extracted with ethyl acetate, and the ethyl acetate layer reduced by heating under reduced pressure to an oil. The oil [Fmoc-Lys(Dnp)] was used without further purification.

Workup

  1. customstored at 4° C
  2. filtrationThe solution was filtered
  3. customDimethoxyethane was removed
  4. temperatureby heating the solution under reduced pressure
  5. extractionThe solution was extracted with ethyl acetate
  6. temperatureby heating under reduced pressure to an oil
  7. customThe oil [Fmoc-Lys(Dnp)] was used without further purification

Sources & evidence

ORD record
ord-b7830d1baddd44a4a70fb1bd3c4e7e8c
Source dataset
uspto-grants-1998_06
Patent number
US05770691

Reaction notes

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