Citric Acid → DTAF lysine

HRID 1154500Notes

Reaction equation

HRID 1154500 reaction equation
[CH:1]1[C:6]([NH:7][C:8]2[N:13]=[C:12]([Cl:14])[N:11]=[C:10]([Cl:15])[N:9]=2)=[CH:5][C:4]2[C:16]([O:18][C:19]3([C:29]4[CH:30]=[CH:31][C:32]([OH:34])=[CH:33][C:28]=4[O:27][C:21]4[CH:22]=[C:23]([OH:26])[CH:24]=[CH:25][C:20]3=4)[C:3]=2[CH:2]=1)=[O:17].CCOC(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O.C([N:57](CC)CC)C>>[CH:1]1[C:6]([NH:7][C:8]2[N:13]=[C:12]([Cl:14])[N:11]=[C:10]([Cl:15])[N:9]=2)=[CH:5][C:4]2[C:16]([O:18][C:19]3([C:29]4[CH:30]=[CH:31][C:32]([OH:34])=[CH:33][C:28]=4[O:27][C:21]4[CH:22]=[C:23]([OH:26])[CH:24]=[CH:25][C:20]3=4)[C:3]=2[CH:2]=1)=[O:17].[NH2:57][C@H:4]([C:16]([OH:18])=[O:17])[CH2:3][CH2:2][CH2:1][CH2:6][NH2:7]

Participants

5

Reactant 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 1239345-((4,6-Dichloro-1,3,5-triazin-2-yl)amino)fluoresceinHCID 12210273Ethanamine, N,N-diethyl-, monohydrate

Product 1

HCID 131714068DTAF lysine

Procedure

α-t-BOC-lysine (1.39 g, 5.64 mmol) was dissolved in 50 ml of 9:1 water-triethylamine, and the solution was cooled to 0° with an ice-water bath. A single portion (1.00 g, 1.88 mmol) of DTAF was added, and the reaction mixture was allowed to stir at 0° for 1.0 hr. The solution was poured into 200 ml of EtOAc, and aqueous citric acid solution was added until the pH of the aqueous phase was approximately 4. The layers were separated, and the aqueous layer was extracted with 100 ml of EtOAc. The combined organic layers were washed with 100 ml of water, dried (MgSO4) and evaporated affording 1.22 g of the DTAF-lysine derivative as an orange foam. The crude product was dissolved in a small volume of MeOH and precipitated by the addition of ether-hexane.

Workup

  1. temperaturethe solution was cooled to 0° with an ice-water bath
  2. additionwas added until the pH of the aqueous phase
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 100 ml of EtOAc
  5. washThe combined organic layers were washed with 100 ml of water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-ef5a2345182c4025a1c8844973a1143b
Source dataset
uspto-grants-1984_12
Patent number
US04489165

Reaction notes

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