Citric Acid → DTAF lysine

HRID 1154500ノート

反応式

HRID 1154500 の反応式
[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]

参加物

5

反応物 4

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

生成物 1

HCID 131714068DTAF lysine

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ef5a2345182c4025a1c8844973a1143b
出典データセット
uspto-grants-1984_12
特許番号
US04489165

反応ノート

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