Dibromomaleimide → Di-dansyl-cystamine maleimide

HRID 929391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929391
[S:1]([N:17]([S:25]([C:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:33]([N:34]([CH3:36])[CH3:35])[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:18][CH2:19][S:20][S:21][CH2:22][CH2:23][NH2:24])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:12])[CH3:11])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].C(C(O)=O)CP(CCC(O)=O)CCC(O)=O.Br[C:58]1[C:63](=[O:64])[NH:62][C:60](=[O:61])[C:59]=1Br.CC([O-])=O.[Na+]>CO>[S:1]([N:17]([S:25]([C:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:33]([N:34]([CH3:36])[CH3:35])[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:26])=[O:27])[CH2:18][CH2:19][S:20][S:21][CH2:22][CH2:23][NH2:24])([C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:9]([N:10]([CH3:11])[CH3:12])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:60]1(=[O:61])[NH:62][C:63](=[O:64])[CH:58]=[CH:59]1

Komponenten

6

Edukt 4

HCID 14279DibromomaleimideHCID 119411Tris(2-carboxyethyl)phosphineHCID 517045Sodium AcetateHCID 86668292Di-dansyl cystamine

Produkt 1

HCID 86668291Di-dansyl-cystamine maleimideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A round bottomed flask was charged with di-dansyl cystamine (100 mg, 0.16 mmol), TCEP (46 mg, 1 eq) and MeOH (10 ml). The reaction mixture was stirred at ambient temperature under argon for 3 hrs. Dibromomaleimide (36 mg, 0.9 eq), in MeOH (5 ml) was then added to the reaction mixture. After 30 mins NaOAc (56 mg, 4 eq), was added to the reaction mixture and the solvent evaporated in vacuo. The residue was worked up with DCM and brine. The organic layers were combined, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, 0-20% EtOAc-DCM) afforded the desired compound as a yellow gum (40 mg, 40%). 1HNMR (CDCl3, 600 MHz), δ8.5 (2H, d J 8.5 Hz aromatic H's), δ8.2 (4H, m aromatic H's), δ7.53 (1H, s CONH), δ7.46 (4H, m, aromatic H's), δ7.1 (2H, d, J=7.4 Hz aromatic H's), δ5.65 (2H, t, J 6.27 SO2NH), δ3.3 (4H, t, J 6.0 SCH2), δ3.17 (4H, q, J 6.0 NHCH2), δ2.8 (12H, s NCH3); 13CNMR (CDCl3, 150 MHz), 6165.9, 152.0, 136.5, 134.7, 130.7, 129.94, 129.85, 129.62, 129.57, 128.63, 123.3, 118.8, 115.4, 45.5, 43.6, 31.8; IR (cm−1) 3288 (br) 1720 (s) MS (Na+) m/z relative intensity: 736 (M, 100); Exact mass calculated for [C32H35N5O6NaS4] requires m/z 736.1368. Found 736.1390 (Na+).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customthe solvent evaporated in vacuo
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica gel, 0-20% EtOAc-DCM)

Quellen und Nachweise

ORD-Eintrag
ord-81423163d5da4e28a6048f46f2c7e8e4
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09295729B2

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